Methyl 4-(benzyloxy)-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate → Methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

HRID 1481145Notes

Reaction equation

HRID 1481145 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:16][CH:17]=2)[CH:12]=[N:11][C:10]=1[C:29]([O:31][CH3:32])=[O:30])C1C=CC=CC=1>CCOC(C)=O.CCO.[Pd]>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)=[CH:16][CH:17]=2)[CH:12]=[N:11][C:10]=1[C:29]([O:31][CH3:32])=[O:30]

Participants

5

Reactant 1

HCID 89812996Methyl 4-(benzyloxy)-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

Product 1

HCID 89813034Methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-(benzyloxy)-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate (200.0 mg, 0.47 mmol) in EtOAc (21 mL) was added a suspension of Pd/C (171.3 mg, 0.16 mmol, 10% by weight) in EtOH (21 mL). The resulting mixture was stirred at room temperature under a hydrogen atmosphere for 16 hours. The resulting suspension was filtered through a pad of celite. The filtrate was concentrated in vacuo and then purified by flash chromatography (0-30% EtOAc/CH2Cl2) to give the title compound in 120.0 mg. 1H NMR (CDCl3, 200 MHz): δ=11.63 (s, 1H), 8.51 (s, 1H), 8.13 (d, 1H, J=9.0 Hz), 7.30 (d, 2H, J=6.6 Hz), 7.06 (d, 1H, J=9.0 Hz), 6.94-6.82 (m, 3H), 4.39 (s, 2H), 4.04 (s, 3H), 3.80 (s, 3H).

Workup

  1. filtrationThe resulting suspension was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by flash chromatography (0-30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-be78f5ec6b26400fb4eedbcf9e803537
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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