HCID 86656614, compound → N-Hydroxy-2-(4-methylbenzoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

HRID 2036876Notes

Reaction equation

HRID 2036876 reaction equation
[CH3:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:18]([NH:20][O:21]C4CCCCO4)=[O:19])=[CH:13][CH:14]=3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1>CO.Cl>[OH:21][NH:20][C:18]([C:12]1[CH:11]=[C:10]2[C:15]([CH2:16][CH2:17][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[CH:29][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH2:9]2)=[CH:14][CH:13]=1)=[O:19]

Participants

4

Reactant 1

HCID 86656614HCID 86656614, compound

Product 1

HCID 44229428N-Hydroxy-2-(4-methylbenzoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamideYield 20%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 70 mg 2-(4-methylbenzoyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide in 6 ml methanol and 6 ml 0.1 N aqueous hydrochloric acid is stirred overnight at ambient temperature. Subsequently, the reaction mixture is evaporated. The residue is dissolved in a mixture of water and acetonitrile and lyophilized. The crude product is further purified by silica gel flash chromatography. 11 mg of the title compound are obtained as colorless solid. MH+=311.1

Workup

  1. customSubsequently, the reaction mixture is evaporated
  2. dissolutionThe residue is dissolved in a mixture of water and acetonitrile
  3. customThe crude product is further purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-360a8039ae954c40bc6d9a9f2299cdc1
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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