Dimethylformamide → Ammonium Hydroxide

HRID 2044195Notes

Reaction equation

HRID 2044195 reaction equation
[Cl:1][C:2]1[C:7](C(O)=[O:9])=[C:6]([F:11])[C:5]([CH3:12])=[CH:4][CH:3]=1.C(Cl)Cl.C(Cl)(=O)C(Cl)=O.C[N:23]([CH:25]=[O:26])C>>[OH-:9].[NH4+:23].[Cl:1][C:2]1[C:7]([C:25]([NH2:23])=[O:26])=[C:6]([F:11])[C:5]([CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 27736696-Chloro-2-fluoro-3-methylbenzoic acid

Product 2

HCID 14923Ammonium HydroxideYield 36%HCID 27736646-Chloro-2-fluoro-3-methylbenzamide

Procedure

To 6-chloro-2-fluoro-3-methylbenzoic acid (10 g, 53 mmol) is added CH2Cl2 (60 mL), DMF (0.5 mL) and oxalyl chloride (9.25 mL, 106 mmol). The reaction mixture is allowed to stir until it reaches homogeneity and is then concentrated in vacuo. The residue is poured onto a 50:50 mixture of ice: 36% ammonium hydroxide to yield 6-chloro-2-fluoro-3-methylbenzamide.

Workup

  1. concentrationis then concentrated in vacuo
  2. additionThe residue is poured onto a 50:50 mixture of ice

Sources & evidence

ORD record
ord-6dc6942cca3b4cc0b730150c345d5ce0
Source dataset
uspto-grants-2013_11
Patent number
US08586782B2

Reaction notes

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