Ethyl 3-hydroxyimino-5-methoxy-1-phenylindene-2-carboxylate → 1-amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19550Notes

Reaction equation

HRID 19550 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[N:23]O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH2:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 73123866Ethyl 3-hydroxyimino-5-methoxy-1-phenylindene-2-carboxylate

Product 1

HCID 116739651-amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Hydroxyimino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (1.00 g, 3.09 mmol) obtained in Step 1 was dissolved in methanol (100 mL), and 10%-palladium (583 mg) was added thereto. The mixture was stirred for 15 hrs at RT while providing H2 gas thereto using a balloon, filtered through celite, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 786 mg of the titled compound (yield: 82%).

Workup

  1. customwhile providing H2 gas
  2. filtrationfiltered through celite
  3. concentrationconcentrated under a reduced pressure
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-840767bf5a6a4b5db2451bd1e7582c14
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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