Ammonium Hydroxide → 2-Chloro-3-nitrobenzamide

HRID 507477Notes

Reaction equation

HRID 507477 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C(Cl)=O.[NH4+:20].[OH-]>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:20])=[O:5]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 198702-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 106795532-Chloro-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

DMF (3 drops) was added to a mixture of 2-chloro-3-nitrobezoic acid (0.99 g, 4.9 mmol), oxalyl chloride (0.47 mL, 5.4 mmol) in CH2Cl2 (20 mL) at 25° C. stirring under N2. After gas formation ceased, all the solid went into solution. After 3 hours the solvent was removed under reduced pressure to leave a light yellow solid which was treated with cold NH4OH (20 mL). 2-Chloro-3-nitrobenzamide was collected as an off-white solid (1.02 g, 100%).

Workup

  1. customAfter 3 hours the solvent was removed under reduced pressure
  2. customto leave a light yellow solid which
  3. custom2-Chloro-3-nitrobenzamide was collected as an off-white solid (1.02 g, 100%)

Sources & evidence

ORD record
ord-01ff3e3ff34c46ae9a7cb2d4b38a5cf6
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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