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1. Single Step

Step Stages Notes Yield

1

1.1R:KOC(Et)Me2, S:PhMe, 5 min, rt

1.2 3 h, rt → 120°C

Schlenk flask used, Reactants: 2,

Reagents: 1, Solvents: 1, Steps: 1,

Stages: 2

Transformations:

1.Reduction of Nitro Compounds to

Amines

2.Reduction of Nitro to Azo

Compounds

30%/

CASREACT ®: Copyright © 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.

3. Single Step

Step Stages Notes Yield

1

1.1R:KOH, C:1687734-51-5, S:Me2CHOH, 24 h,

80°C

Schlenk tube used, conversion of azo

derivative = 7%, conversion of aniline =

93%, alternative reaction conditions

shown, Reactants: 1, Reagents: 1,

Catalysts: 1, Solvents: 1, Steps: 1,

Stages: 1

Transformations:

1.Reduction of Nitro Compounds to

Amines

2.Reduction of Nitro to Azo

Compounds

CASREACT ®: Copyright © 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.

4. Single Step

Step Stages Notes Yield 1

1.1R:KOH, C:1974333-28-2, S:Me2CHOH, 24 h,

80°C

Schlenk tube used, conversion of aniline

= 80%, conversion of azo derivative =

3%, conversion of azoxy derivative =

17%, catalyst prepared and used,

alternative reaction conditions shown,

Reactants: 1, Reagents: 1, Catalysts: 1,

Solvents: 1, Steps: 1, Stages: 1

Transformations:

1.Reduction of Nitro Compounds to

Amines

2.Reduction of Nitro to Azo

Compounds

3.Reduction of Nitro to Azoxy

Compounds

CASREACT ®: Copyright © 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.5. Single Step

Step Stages Notes

Yield 1

1.1

R:KNO 3, R:HfCl 4 R:

R:Quinoline, S:H 2O, rt → 65°C; 3 h, 65°C

Reactants: 1, Reagents: 4, Solvents: 1,Steps: 1, Stages: 1Transformation:

1.Dimerization of Diazonium Salts

92%

CASREACT ®: Copyright © 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.