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Potassium Carbonate → 4-(2-Chloroethylamino)-3-nitro-benzoic Acid Methyl Ester

HRID 555289
Notes
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Reaction equation

HRID 555289 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[Cl:22][CH2:23][CH2:24][NH2:25]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:25][CH2:24][CH2:23][Cl:22])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 122573344-(2-Chloroethylamino)-3-nitro-benzoic Acid Methyl EsterYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-3-nitro-benzoic acid methyl ester (10.0 g, 0.0502 mol) in dry DMF (100 mL) was added with stirring potassium carbonate (59.0 g, 0.43 mol) followed by 2-chloroethylamine hydrochloride (8.7 g, 0.075 mol) and the mixture was stirred for 15 h at ambient temperature. The reaction mixture was diluted with ice water (500 mL) and the solid precipitated was filtered, washed with water and dried under vacuum to get a yellow solid (12.7 g, 98%). MS-ESI m/z 259 (M+1).

Workup

  1. customthe solid precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-77dd8b5c7214480c8aa98c17cb8f4198
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053431B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes