Pentanal → HCID 69155737, compound

HRID 750194Notes

Reaction equation

HRID 750194 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH2:23])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4].C(N(CC)CC)C.[CH:31](=O)[CH2:32][CH2:33][CH2:34][CH3:35]>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([N:23]=[CH:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 8063PentanalHCID 8471TriethylamineHCID 69156379HCID 69156379, compound

Product 1

HCID 69155737HCID 69155737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-amino-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (210 mg), triethylamine (130 μl), valeraldehyde (81 μl) and methanol (4.2 ml) was stirred at 70° C. for 3.5 hrs. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1) to give the title compound (200 mg) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1)

Sources & evidence

ORD record
ord-c11eb30887784b50a96001acae14f089
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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