4-Aminophenylacetic acid → HCID 67021624, compound

HRID 1660965Notes

Reaction equation

HRID 1660965 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1.[F-].[K+]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:17]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 145334-Aminophenylacetic acidHCID 738951-Fluoro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 67021624HCID 67021624, compound

Conditions

Temperature
170 °C

Procedure

A mixture of 2-nitrofluorobenzene (1.5 mL, 14.2 mmol, 1.5 equiv) (Aldrich), 4-aminophenyl acetic acid (1.44 g, 9.5 mmol), and KF (0.550 g, 9.5 mmol) is stirred at 170° C. for 16 h in a sealed tube. The reaction mixture is then allowed to cool to rt, triturated in CH2Cl2/MeOH (95:5) and filtered, and the filtrate is concentrated. The residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 97:3→95:5) to provide the title compound as a red solid: ES-MS: 273.0 [M+H]+; single peak at tR=4.44 min (System 1); Rf=0.20 (CH2Cl2/MeOH, 95:5).

Workup

  1. temperatureto cool to rt
  2. customtriturated in CH2Cl2/MeOH (95:5)
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated
  5. customThe residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 97:3→95:5)

Sources & evidence

ORD record
ord-8ca2a94d7e9344c6ba77a4cba711b611
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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