HCID 68917915, compound → HCID 68915072, compound

HRID 1958516Notes

Reaction equation

HRID 1958516 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:7]([C:22]([OH:24])=[O:23])=[CH:6]2>C(O)C.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH:7]([C:22]([OH:24])=[O:23])[CH2:6]2

Participants

4

Reactant 1

HCID 68917915HCID 68917915, compound

Product 1

HCID 68915072HCID 68915072, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-methoxy-1-(4′-methoxybenzoyl)-1H-indole-2-carboxylic acid (7.02 g, 21.57 mmol) in ethanol (200 mL) was added platinum oxide (0.7 g). The mixture was hydrogenated for 6 hours at 32 psi. The reaction mixture was filtered through a pad of Celite. The filter cake was washed with ethanol. The combined filtrate and washings was evaporated in vacuo to dryness. The solid residue was recrystallized from ethanol to yield 5-methoxy-1-(4′-methoxybenzoyl)-2,3-dihydro-1H-indole-2-carboxylic acid, 6.35 g (90%): mp 151-152° C.; 1H NMR (DMSO-d6) δ 3.05 (1H, m, CH), 3.56-3.63 (1H, m, N—CH), 3.70 (3H, s, OMe), 3.81 (3H, s, OMe), 4.97-5.01 (1H, m, CH), 6.67 (1H, br, ArH), 6.86 (2H, m, 2×ArH), 7.00 (2H, d, J=8.6 Hz, 2×H), 7.45 (2H, J=8.6 Hz, 2×ArH), 12.92 (1H, brs, exchangeable, OH). Anal. Calcd. for C18H17NO5.0.1H2O: C, 65.69; H, 5.26; N, 4.25. Found: C, 65.61; H, 5.48; N, 4.17.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washThe filter cake was washed with ethanol
  3. customThe combined filtrate and washings was evaporated in vacuo to dryness
  4. customThe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8ec2711856f14040addf93931cfb8964
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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