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1-Butanol → 4-Hydroxy-1-oxo-6-(4-propoxy-phenoxy)-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester

HRID 2077196
Notes
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Reaction equation

HRID 2077196 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=3)[CH:12]=2)[C:7]1=[O:27])[CH3:2].[O-][CH2:30][CH2:31]CC.[Na+].C(O)CCC.Cl>>[CH2:1]([O:3][C:4]([C:5]1[NH:6][C:7](=[O:27])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=1)=[CH:10][CH:9]=2)=[O:28])[CH2:2][CH2:30][CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 23669364Sodium n-butylateHCID 67110548[1,3-Dioxo-5-(4-propoxy-phenoxy)-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester

Product 1

HCID 671101594-Hydroxy-1-oxo-6-(4-propoxy-phenoxy)-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester

Procedure

A mixture of [1,3-dioxo-5-(4-propoxy-phenoxy)-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester (2.485 g, 6.48 mmol), sodium butoxide, and butanol (14.3 mmol, 27 mL butanol) was heated at 90° C. to 100° C. for 2 h. Then the reaction mixture was allowed to cool to ambient temperature, acidified with 2 M HCl to pH 3-4, and extracted with EtOAc. The organic phase was then washed with water and saturated NaCl solution, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (722 mg). ESI MS (m/z): 412 (M+H)+.

Workup

  1. temperaturewas heated at 90° C. to 100° C. for 2 h
  2. extractionextracted with EtOAc
  3. washThe organic phase was then washed with water and saturated NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-750fad2672774143b92a9ca79d40c1bb
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928120B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes