Acetic Acid → N-(4-chlorophenyl)benzene-1,2-diamine

HRID 1019846Notes

Reaction equation

HRID 1019846 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-])=O)=[CH:4][CH:3]=1.CC(O)=O>C(Cl)Cl.[Zn]>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89958N-(4-chlorophenyl)-2-nitroaniline

Product 1

HCID 522323N-(4-chlorophenyl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloroanilino)-nitrobenzene (57.0 g) in CH2Cl2 (40 mL) was added AcOH (90 mL), then Zn powder (105 g) was added in small portions. After Zn powder was added, the color of the mixture became light green, filtered by suction, washed with CH2Cl2. The filtrate was concentrated to dryness. Water was added, filtered, and washed with water to give a brown solid. This solid was used directly in the next step without further purification.

Workup

  1. filtrationfiltered by suction
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate was concentrated to dryness
  4. additionWater was added
  5. filtrationfiltered
  6. washwashed with water
  7. customto give a brown solid
  8. customThis solid was used directly in the next step without further purification

Sources & evidence

ORD record
ord-dbdc99b91d4c43babbff577c53474c92
Source dataset
uspto-grants-2014_05
Patent number
US08716292B2

Reaction notes

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