Methylamine → 5-Fluoro-N-methyl-2-nitrobenzamide

HRID 77370Notes

Reaction equation

HRID 77370 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH:14]([N:17](CC)C(C)C)(C)C.CN.O1CCCC1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(OCC)(=O)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH:17][CH3:14])=[O:8]

Participants

8

Reactant 6

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 442030775-Fluoro-N-methyl-2-nitrobenzamideYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-fluoro-2-nitrobenzoic acid (0.5 g, 2.7 mmol) in dichloromethane (10 mL) was cooled with an ice water bath before the addition of N,N-diisopropylethylamine (1.13 g, 8.1 mmol). To this solution 2M methylamine in tetrahydrofuran (1.6 g, 3.24 mmol) was added dropwise over 5 minutes. 1-Propanephosphonic acid cyclic anhydride as a 50% wt solution in ethyl acetate (2.56 mL, 4.05 mmol) was added dropwise. The ice bath was then removed and stirring continued overnight. The mixture was purified on a 2 g ABW column to afford 5-fluoro-N-methyl-2-nitrobenzamide (0.26 g, 1.31 mmol).

Workup

  1. customThe ice bath was then removed
  2. customThe mixture was purified on a 2 g ABW column

Sources & evidence

ORD record
ord-0444badd0240430d86c19824a4dbecc0
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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