Ethyl Acetate → 4-(6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]inden-10-yl)-phenol

HRID 2251105Notes

Reaction equation

HRID 2251105 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]3[C:20]([N:21]=[C:22]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]=24)=[CH:19][CH:18]=[N:17]3)=[CH:11][CH:10]=1)C1C=CC=CC=1.CCOC(C)=O>CO.[Pd]>[N:17]1[N:16]2[C:20]([N:21]=[C:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[C:15]2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 5858771710-(4-benzyloxy-phenyl)-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene

Product 1

HCID 1360572464-(6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]inden-10-yl)-phenolYield 79.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10-(4-Benzyloxy-phenyl)-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (100 mg, 0.27 mmol) was dissolved in CH3OH (5 mL) and EtOAc (2 mL) followed by the addition of palladium (10% by weight on carbon, 5 mg). The resulting mixture was stirred under a hydrogen atmosphere (balloon) at room temperature overnight. The catalyst was filtered off and the filtrate concentrated to give 4-(6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]inden-10-yl)-phenol as a colorless solid (60 mg, 79% yield).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-48ac228c83a342959844767106698b7f
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

Loading…