Hydrochloric Acid → HCID 10217426, compound

HRID 750285Notes

Reaction equation

HRID 750285 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([O:34]C)=[O:33])=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([OH:34])=[O:33])=[CH:30][CH:31]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69155462HCID 69155462, compound

Product 1

HCID 10217426HCID 10217426, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-chloro-4-(3-hydroxymethylphenyl)-2-(4-methoxycarbonylbenzyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (130 mg) in methanol (4.0 ml) was added 1N sodium hydroxide (390 μl), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH 3 with 1N hydrochloric acid and concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1) to give the title compound (92 mg) as a colorless powder. 1H-NMR (CDCl3) δ: 3.23 (3H, s), 4.76 (2H, s), 5.41 (1H, d, J=15.6 Hz), 5.48 (1H, d, J=15.6 Hz), 7.18-7.30 (3H, m), 7.35 (2H, d, J=8.7 Hz), 7.42-7.47 (2H, m), 7.52 (1H, dd, J=2.1, 8.4 Hz), 8.02 (2H, d, J=8.7 Hz), 8.48 (1H, d, J=8.4 Hz). HPLC analysis: purity 97.9% (retention time: 3.84 min). MS (ESI+): 478 (M+H), 480.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-f8bfa31626164445bce56b18caf38f1b
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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