Methyl 4-aminobenzoate → HCID 608483, compound

HRID 274589Notes

Reaction equation

HRID 274589 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1>C(O)(=O)C.O>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

5

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 608483HCID 608483, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 4-aminobenzoate (7.6 g) in acetic acid (25 ml) was added 2,5-dimethoxytetrahydrofuran (6.6 g) dropwise and the reaction mixture was heated under reflux for 1 hour and then diluted with water. The resulting precipitated crystals were purified by column chromatography on silica gel. Recrystallization from ethyl acetate-hexane afforded the title compound as colorless plates (7.5 g, 74%), m.p. 128°-129° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe resulting precipitated crystals
  4. customwere purified by column chromatography on silica gel
  5. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-42671448df174bff8630eb7219a8156d
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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