Dimethylformamide → Ammonium Hydroxide

HRID 1811534Notes

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

Reactant 4

HCID 6228Dimethylformamide

HCID 6344Dichloromethane

HCID 65578Oxalyl chloride

HCID 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

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

Sources & evidence

ORD record: ord-36a79107114642328e54f2ecccfbd40d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362294B2

Reaction notes

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