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Acetic Acid → 2-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

HRID 907278
Notes
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Reaction equation

HRID 907278 reaction equation
[CH2:1]([N:8]1[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:22]3[CH:27]=[C:26]([C:28](=[O:33])[NH:29][CH:30]4[CH2:32][CH2:31]4)[CH:25]=[CH:24][C:23]=3[CH3:34])[CH:14]=2)[C:9]1=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C.O>CO>[CH2:1]([N:8]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:22]3[CH:27]=[C:26]([C:28](=[O:33])[NH:29][CH:30]4[CH2:31][CH2:32]4)[CH:25]=[CH:24][C:23]=3[CH3:34])[CH:14]=2)[C:9]1=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 575517342-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Product 1

HCID 575517272-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the product of step ii) (0.88 g) and 5N sodium hydroxide (2.3 mL) in methanol (20 mL) was heated at 50° C. for 2 hours and then allowed to cool to room temperature. The reaction mixture was treated with glacial acetic acid (1 mL) and then water (20 mL). The precipitate was collected by filtration, washed with water and dried under vacuum to afford the sub-title compound (0.77 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-66d17a2ef5894c0789da002983f94c2f
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012979B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes