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Methanol → HCID 18399215, compound

HRID 1019370
Notes
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Reaction equation

HRID 1019370 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:30]3[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=3)=[C:14]([C:26]([O:28][CH3:29])=[O:27])[N:15]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[C:16]2=[O:19])=[CH:11][C:10]=1[O:42][CH3:43])C1C=CC=CC=1.CO>[C].[Pd].CN(C)C=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:30]3[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=3)=[C:14]([C:26]([O:28][CH3:29])=[O:27])[N:15]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[C:16]2=[O:19])=[CH:11][C:10]=1[O:42][CH3:43]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 887MethanolHCID 18399330HCID 18399330, compound

Product 1

HCID 18399215HCID 18399215, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To the compound obtained in Example 1 (2.8 g) are added methanol (100 ml), dimethylformamide (100 ml) and palladium-carbon (100 mg), and the mixture is stirred under hydrogen atmosphere (1 atm) at room temperature for 1.5 hour. The catalyst is removed by filtration, and the filtrate is concentrated. The precipitated crystals are collected by filtration, and washed with diethyl ether to give 7-hydroxy-6-methoxy-3-methoxycarbonyl-2-morpholino-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (2.26 g) as listed in Table 1.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-478bbd789fe24d5db67ba59443b47364
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06486155B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes