HCID 70445087, compound → HCID 20194696, compound

HRID 653435Notes

Reaction equation

HRID 653435 reaction equation
C1(C[O:8][C:9](=[O:31])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[N:18]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:17](=[O:30])[CH2:16]3)C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:18]2[C:19]3[C:15](=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10][C:9]([OH:31])=[O:8])[CH2:16][C:17]2=[O:30])=[O:29])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 70445087HCID 70445087, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20194696HCID 20194696, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 29.5 g (0.1 mole) 2,3-dihydro-1-(4-methoxybenzoyl)-2-oxo-1H-indole-7-acetic acid phenylmethyl ester in tetrahydrofuran is reduced with hydrogen over 2 g of 20% Pd/C catalyst. After the theoretically calculated amount of hydrogen has been consumed, the solution is filtered through filter aid. The filtrate is concentrated at reduced pressure and the oily residue is triturated with anhydrous diethyl ether to yield 2,3-dihydro-1-(4-methoxybenzoyl)-2-oxo-1H-indole-7-acetic acid.

Workup

  1. customAfter the theoretically calculated amount of hydrogen has been consumed
  2. filtrationthe solution is filtered
  3. filtrationthrough filter aid
  4. concentrationThe filtrate is concentrated at reduced pressure
  5. customthe oily residue is triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-fd3d1f20dcbe4d8abee03d4ceadf3d5a
Source dataset
uspto-grants-1987_06
Patent number
US04677112

Reaction notes

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