Formic Acid → N-(2-bromo-5-nitrophenyl)formamide

HRID 2374173Notes

Reaction equation

HRID 2374173 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].O.[CH:13](O)=[O:14]>>[CH:13]([NH:4][C:3]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=1[Br:1])=[O:14]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 826072-Bromo-5-nitroaniline

Product 1

HCID 350130N-(2-bromo-5-nitrophenyl)formamideYield 98%

Procedure

A solution of 2-bromo-5-nitroaniline (5.27 g, 24.3 mmol) in 98% formic acid (30 ml) was heated to reflux for 90 min under nitrogen. The cooled reaction mixture was then poured into cold water (600 ml) which afforded a yellow precipitate. The solid was isolated by filtration and the cake washed with cold water (2×200 ml). Subsequent drying overnight under vacuum overnight afforded N-formyl-2-bromo-5-nitroaniline (5.84 g, 98%) as a yellow solid: 1H NMR (DMSO-d6) δ 10.14 (br s, 1H), 9.01 (d, J=2.4 Hz, 1H), 8.46 (s, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.91 (dd, J=8.8, 2.5 Hz, 1H); 13C NMR (DMSO-d6) δ 161.2, 146.9, 136.6, 134.0, 120.6, 119.8, 116.7.

Workup

  1. temperatureto reflux for 90 min under nitrogen
  2. customThe cooled reaction mixture
  3. customafforded a yellow precipitate
  4. customThe solid was isolated by filtration
  5. washthe cake washed with cold water (2×200 ml)
  6. customSubsequent drying overnight under vacuum overnight

Sources & evidence

ORD record
ord-43537d1ab2f345f0b3603a07ebbbdd06
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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