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

HRID 706203Notes

Reaction equation

HRID 706203 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]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 23669364Sodium n-butylateHCID 67110548HCID 67110548, compound

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-b66f87b8849c471991d9cb7ac0e95243
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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