2-Chloro-4-benzylnitrobenzene → 2-Chloro-4-benzylaniline

HRID 1062405Notes

Reaction equation

HRID 1062405 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-])=O>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[NH2:15]

Participants

4

Reactant 1

HCID 222871592-Chloro-4-benzylnitrobenzene

Product 1

HCID 222873452-Chloro-4-benzylanilineYield 44.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-4-benzylnitrobenzene (Method 29) (0.60 g) in ethyl acetate was treated with 10% Pd/C (0.06 g) under argon. The mixture was then stirred under a hydrogen atmosphere for 10 hours. The mixture was filtered under argon and extracted with aqueous hydrochloric acid (50% v/v, 50 ml). The aqueous layer was separated, basified with 2M aqueous NaOH and extracted with ethyl acetate to give the title compound as an oil (0.237 g). NMR: 3.6 (s, 2H), 5.1 (brs, 2H), 6.7 (d, 1H), 6.9 (dd, 1H), 7.0 (d, 1H), 7.1-7.3 (m, 5H); MS (CI): 218 (M+)

Workup

  1. filtrationThe mixture was filtered under argon
  2. extractionextracted with aqueous hydrochloric acid (50% v/v, 50 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-c82182cf75624048a37748d56bbe690a
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

Loading…