4-[(3-Fluorophenyl)amino]-3-nitrobenzoic acid → HCID 54887667, compound

HRID 1723864Notes

Reaction equation

HRID 1723864 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[N+:18]([O-])=O)[CH:5]=[CH:6][CH:7]=1>C1COCC1.[Pd]>[NH2:18][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 160017004-[(3-Fluorophenyl)amino]-3-nitrobenzoic acid

Product 1

HCID 54887667HCID 54887667, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-fluorophenylamino)-3-nitrobenzoic acid (5.57 g, 20.1 mmol) in THF (100 mL) was charged with 10% Pd/C (500 mg) and the reaction flask evacuated and subsequently charged with H2(g) three times. The mixture was stirred vigorously for 12 h after which it was filtered through diatomaceous earth and the filtrate concentrated in vacuo to give 3-amino-4-(3-fluorophenylamino)benzoic acid as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.34 (d, J=2.0 Hz, 1H), 7.19-7.13 (m, 2H), 7.08 (d, J=8.4 Hz, 1H), 6.70 (d, J=8.0 Hz, 1H), 6.60 (d, J=11.6 Hz, 1H), 6.54 (t, J=8.4 Hz, 1H), 5.02 (b, 1H); MS (ES+): m/z 247 [MH+].

Workup

  1. customthe reaction flask evacuated
  2. additionsubsequently charged with H2(g) three times
  3. filtrationwas filtered through diatomaceous earth
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-68fffeefcf9a46afaf6642915624dd95
Source dataset
uspto-grants-2009_02
Patent number
US07485658B2

Reaction notes

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