4-Aminobenzoic Acid → Ethyl 3-[4-(carboxy)phenylamino]propionate

HRID 1601096Notes

Reaction equation

HRID 1601096 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>C(O)(=O)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][CH2:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 8821Ethyl Acrylate

Product 1

HCID 21830455Ethyl 3-[4-(carboxy)phenylamino]propionateYield 63.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-aminobenzoic acid (6.85 g, 0.05 mol) and ethyl acrylate (15 g, 0.15 mol) in acetic acid (40 mL) was heated to 100° C. for 15 h. The solid which formed was filtered, washed with hexane and dried to give the title compound (7.5 g, 63%).

Workup

  1. customThe solid which formed
  2. filtrationwas filtered
  3. washwashed with hexane
  4. customdried

Sources & evidence

ORD record
ord-4f45e341d1144e75b9f7619547af73bf
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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