alpha-Benzamido(2,3-dihydro-5-benzofuranyl)acetic acid → 2-Amino-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acid

HRID 904018Notes

Reaction equation

HRID 904018 reaction equation
C([NH:9][CH:10]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][CH2:20][CH2:19][C:18]=2[CH:22]=1)[C:11]([OH:13])=[O:12])(=O)C1C=CC=CC=1.[H][H]>CO.O.[Pd]>[NH2:9][CH:10]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][CH2:20][CH2:19][C:18]=2[CH:22]=1)[C:11]([OH:13])=[O:12]

Participants

6

Reactant 2

HCID 23335824alpha-Benzamido(2,3-dihydro-5-benzofuranyl)acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 205312232-Amino-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acidYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The α-benzamido(2,3-dihydro-5-benzofuranyl)acetic acid (100 mg) is dissolved in 20 ml of methanol and 40 ml of water. Then 20 mg of a palladium on carbon catalyst is added and the mixture subjected to hydrogen pressure of 10 to 40 pounds/in2 for 4 hours. The mixture is filtered to remove the solid and the methanol is evaporated to give the title compound in about 60% yield. NMR(DMSO-D6)ppm(δ)7.95(s,1);6.7(m,3); 4.8(s,1);4.42(t,2);2.95(t,2).

Workup

  1. customin2 for 4 hours
  2. filtrationThe mixture is filtered
  3. customto remove the solid
  4. customthe methanol is evaporated

Sources & evidence

ORD record
ord-e5b608ea5b7742c6a9168fd4f219f288
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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