HCID 14838655, compound → 5-Amino-2,3-dihydro-1-benzofuran-7-carboxylic acid

HRID 2098391Notes

Reaction equation

HRID 2098391 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[C:7]2[O:8][CH2:9][CH2:10][C:6]=2[CH:5]=1)([O-])=O>CO>[NH2:1][C:4]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[C:7]2[O:8][CH2:9][CH2:10][C:6]=2[CH:5]=1

Participants

3

Reactant 1

HCID 14838655HCID 14838655, compound

Product 1

HCID 160423025-Amino-2,3-dihydro-1-benzofuran-7-carboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid was dissolved in the minimum amount of methanol (1.3 L) and nitrogen was bubbled through the solution for 20 minutes. A mixture of 5% palladium on charcoal (1.0 g) in water (20 ml) was added and the mixture loaded into a 2 L autoclave. After 2 sequential evacuation-N2 purges the vessel was charged to 5 bar H2 and stirred for 4 days. The mixture was flushed with nitrogen, filtered through celite and concentrated to give 5-amino-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.5 g, 19.5 mmol, 63% over 2 steps)

Workup

  1. customwas bubbled through the solution for 20 minutes
  2. additionA mixture of 5% palladium on charcoal (1.0 g) in water (20 ml)
  3. additionwas added
  4. additionwas charged to 5 bar H2
  5. customThe mixture was flushed with nitrogen
  6. filtrationfiltered through celite and
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0afc42af37b64e8699a02d3d22232690
Source dataset
uspto-grants-2013_05
Patent number
US08450506B2

Reaction notes

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