p-Aminophenylacetic acid ethyl ester → HCID 67021331, compound

HRID 1660974Notes

Reaction equation

HRID 1660974 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1)[CH3:13]>CN1C(=O)CCC1.CCOC(C)=O.O>[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[N+:9]([O-:11])=[O:10])=[CH:21][CH:22]=1)[CH3:13]

Participants

6

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 67021331HCID 67021331, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-bromo-4-fluoro-3-nitrobenzene (MATRIX SCIENTIFIC) (10.7 g, 48.7 mmol) and 4-aminophenylacetic acid ethyl ester (8.7 g, 48.7 mmol) in NMP (50 mL) is stirred for 48 h at 110° C. The reaction mixture is allowed to cool at rt, diluted with EtOAc and H2O. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed brine, dried (Na2SO4), filtered and concentrated. Silica gel column chromatography purification (Hexane/EtOAc, 4:1) of the crude product affords the title compound as an orange oil: ES-MS: 380.9 [M+2]+; single peak at tR=5.75 min (System 1); Rf=0.27 (Hexane/EtOAc, 4:1).

Workup

  1. temperatureto cool at rt
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with EtOAc
  4. washThe combined organic phase is washed brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customSilica gel column chromatography purification (Hexane/EtOAc, 4:1) of the crude product

Sources & evidence

ORD record
ord-bd1e9f57df68422d926a48f2246c77d7
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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