1-Butanol → HCID 14883410, compound

HRID 1618263Notes

Reaction equation

HRID 1618263 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]2[C:14]([C:15]=1[O:16]C(=O)C)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].CCCCO.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 12424768HCID 12424768, compound

Product 1

HCID 14883410HCID 14883410, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-acetoxy-1-phenyl-isoquinoline-3-carboxylic acid ethyl ester (671 mg, 2 mmol; can be obtained according to D. A. Walsh et al. in J. Med. Chem. 1978, 21, 582-585), n-BuOH (60 ml) and concentrated H2SO4 (1.7 ml) was refluxed with stirring for 4 h before the reaction mixture was added to concentrated aqueous NaHCO3 solution (60 ml) with stirring. Then EtOAc (120 ml) was added and the mixture was stirred vigorously for 15 min. Subsequently, the organic phase was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel using hexanes:EtOAc=95:5 as the eluent gave the title compound as a solid (126 mg); 1H NMR (CDCl3): δ=11.96 (s, 1H), 8.44 to 8.49 (m, 1H), 8.01 to 8.05 (m, 1H), 7.43 to 7.80 (m, 7 H), 4.56 (q, 2 H), 1.49 (t, 3 H).

Workup

  1. customcan be obtained
  2. stirringwith stirring
  3. stirringthe mixture was stirred vigorously for 15 min
  4. customSubsequently, the organic phase was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-216c63ed60804a23a8848da51f92bfa0
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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