4-Aminophenylacetic acid → HCID 67021624, compound

HRID 1010722Notes

Reaction equation

HRID 1010722 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 1.5 ml of 2-nitrofluorobenzene (Aldrich), 1.44 g of 4-aminophenyl acetic acid and 0.550 g of KF is stirred at 170° C. for 16 hours in a sealed tube. The mixture obtained is allowed to cool to rt, triturated in CH2Cl2/MeOH (95:5) and filtered. The filtrate obtained is concentrated and the concentrate obtained is purified by silica gel column chromatography. [4-(2-Nitro-phenylamino)-phenyl]-acetic acid is obtained in the form of a 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. customThe mixture obtained
  2. temperatureto cool to rt
  3. customtriturated in CH2Cl2/MeOH (95:5)
  4. filtrationfiltered
  5. customThe filtrate obtained
  6. concentrationis concentrated
  7. customthe concentrate obtained
  8. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee93fe5c6c454020964361fb7fd60282
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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