Acetic Acid → HCID 18925359, compound

HRID 21540Notes

Reaction equation

HRID 21540 reaction equation
C(C1[CH:4]=[C:5]2[C:10](=[C:11]3[S:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:12]=13)[CH:9]=[N:8][CH:7]=[CH:6]2)#N.[OH-].[K+].[C:22]([OH:25])(=[O:24])[CH3:23]>OCC(CO)O.O>[C:22]([C:23]1[CH:4]=[C:5]2[C:10](=[C:11]3[S:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:12]=13)[CH:9]=[N:8][CH:7]=[CH:6]2)([OH:25])=[O:24]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 304619[1]Benzothiolo[3,2-h]isoquinoline-6-carbonitrile

Product 1

HCID 18925359HCID 18925359, compound

Reagents, catalysts & solvents 2

HCID 753GlycerolSolventHCID 962WaterSolvent

Procedure

One hundred thirty mg (0.5 mM) of 6-cyanobenzothieno[3,2-h]isoquinoline (4), prepared in Example 1, was suspended in a hot solution of 168 mg (3 mM) KOH in 1 ml glycerine. The reaction mixture was stirred and heated at 160° C.-170° C. overnight. The resulting yellow solution was cooled, diluted with water and made slightly acidic with glacial acetic acid. A yellow precipitate was collected, washed with water, and air dried to yield 120 mg of product. This initial product was recrystallized from a mixture of DMSO and water to give 78 mg product, mp greater than about 305° C. This then was dried at 80° C./0.2 mm overnight, and characterized as compound 6 using I.R. and mass spectrometry.

Workup

  1. temperatureheated at 160° C.-170° C. overnight
  2. temperatureThe resulting yellow solution was cooled
  3. customA yellow precipitate was collected
  4. washwashed with water, and air
  5. customdried

Sources & evidence

ORD record
ord-5c250430b529499aa12d2ccbd03a77bb
Source dataset
uspto-grants-1995_06
Patent number
US05424315

Reaction notes

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