Hydrochloric Acid → 4-Amino-2,3-difluoro-5-nitrobenzoic acid

HRID 992385Notes

Reaction equation

HRID 992385 reaction equation
[N+:1]([C:4]1[C:5](F)=[C:6]([F:14])[C:7]([F:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-:3])=[O:2].Cl.[OH-].[NH4+:18]>>[NH2:18][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:13])[C:6]=1[F:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 158712412,3,4-Trifluoro-5-nitrobenzoic acid

Product 1

HCID 162440884-Amino-2,3-difluoro-5-nitrobenzoic acidYield 64%

Procedure

Solid 5-nitro-2,3,4-trifluorobenzoic acid (0.75 g, 0.00339 mol) was dissolved in concentrated ammonium hydroxide (25 ml) to give instantly a yellow solution. A precipitate began to form within five minutes, after which time the mixture was acidified to pH 0 with concentrated aqueous hydrochloric acid. A yellow precipitate rapidly formed. The mixture was heated to boiling and was filtered hot. The yellow solids were washed with 10% aqueous hydrochloric acid and were suction dried to afford 0.47 g of a yellow powder; 64% yield; 1H-NMR (400 MHz; DMSO) δ13.32 (s, 1H), 8.36 (d, 1H, J=7.6 Hz), 7.98 (s, 2H); 19F-NMR (376 MHz; DMSO) δ−128.69 to −128.76 (m), −153.60 (d).

Workup

  1. customto give instantly a yellow solution
  2. customto form within five minutes
  3. customA yellow precipitate rapidly formed
  4. temperatureThe mixture was heated
  5. filtrationwas filtered hot
  6. washThe yellow solids were washed with 10% aqueous hydrochloric acid
  7. customdried

Sources & evidence

ORD record
ord-bea972289b4f4465abbdd39689062bc2
Source dataset
uspto-grants-2002_10
Patent number
US06469004B1

Reaction notes

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