Ethyl Acetate → N-(6-mercaptoisoquinolin-1-yl)benzamide

HRID 1366745Notes

Reaction equation

HRID 1366745 reaction equation
[OH-].[Na+].[C:3]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]C(=O)N(C)C)=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O.O.CO.C1COCC1.CCCCCCC>[SH:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:12]([NH:11][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[N:13][CH:14]=[CH:15]2

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86612976dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester

Product 1

HCID 136378996N-(6-mercaptoisoquinolin-1-yl)benzamideYield 53.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolventHCID 447138Water dimerSolvent

Procedure

A solution of NaOH (92 mg) in water H2O (1 ml) was added to a solution of dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester (70 mg) in MeOH (1 ml) and THF (1 ml). The mixture was stirred for 1 h at ambient temperature then for a further 1 h at 56° C. The organics were removed in vacuo then the mixture was diluted with water and acidified with dilute hydrochloric acid (pH˜3.5). The mixture was extracted with ethyl acetate (X3), dried (sodium sulphate) and concentrated in vacuo to give a residue. Flash chromatography of the residue (eluent: 1-5% ethyl acetate in heptane) gave N-(6-mercaptoisoquinolin-1-yl)-benzamide (30 mg).

Workup

  1. waitfor a further 1 h at 56° C
  2. customThe organics were removed in vacuo
  3. additionthe mixture was diluted with water
  4. extractionThe mixture was extracted with ethyl acetate (X3)
  5. dry with materialdried (sodium sulphate)
  6. concentrationconcentrated in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-1f4c81053dbd453ebe5b477757186187
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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