Benzocaine → Ethyl 4-[(2-nitrophenyl)amino]benzoate

HRID 1675772Notes

Reaction equation

HRID 1675772 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]>>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 2337BenzocaineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 11208411Ethyl 4-[(2-nitrophenyl)amino]benzoate

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 4-aminobenzoate (1.00 g, 6.05 mmol) and 2-fluoronitrobenzene (0.64 mL, 6.05 mmol) was heated at 160° C. for 18 h. The crude product was purified by silica gel chromatography, eluting with hexane:EtOAc-70:30, to give the title compound. MS: m/z=287 (M+1).

Workup

  1. customThe crude product was purified by silica gel chromatography
  2. washeluting with hexane

Sources & evidence

ORD record
ord-d3a45cf1f99c47a6b1f94e3b3b1a94ed
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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