Sulfuric Acid → HCID 5274983, compound

HRID 21539Notes

Reaction equation

HRID 21539 reaction equation
[C:1]([C:3]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)#[N:2].S(=O)(=O)(O)[OH:21].[OH-].[NH4+]>O>[CH:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]([NH2:2])=[O:21])=[C:12]3[C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=4[S:15][C:11]3=2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 304619[1]Benzothiolo[3,2-h]isoquinoline-6-carbonitrile

Product 1

HCID 5274983HCID 5274983, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Two hundred mg of 6-cyanobenzothieno[3,2-h]isoquinoline (4), prepared in the preceding Example, was mixed with a solution of 2 ml water and 3 ml concentrated sulfuric acid. The reaction mixture was heated at 110° C.-120° C., and gave rise to a yellowish brown solution. After heating for approximately 5 hr, when TLC indicated the absence of starting material, the reaction mixture was poured onto 40 ml ice and water. The yellow solution thus obtained was made alkaline (to a pH of about 8) with concentrated ammonium hydroxide. The gray flocculent solid that precipitated was collected and washed with water to yield 130 mg dried product. This material was recrystallized from 75 ml CHCl3, to give 85 mg of a white solid, m.p. 295° C.-302° C., characterized as compound 5 by I.R. and mass spectrometry.

Workup

  1. temperatureThe reaction mixture was heated at 110° C.-120° C.
  2. customgave rise to a yellowish brown solution
  3. temperatureAfter heating for approximately 5 hr
  4. customThe yellow solution thus obtained
  5. customThe gray flocculent solid that precipitated
  6. customwas collected
  7. washwashed with water

Sources & evidence

ORD record
ord-d497204f0c944710930cac2bf90ec2cf
Source dataset
uspto-grants-1995_06
Patent number
US05424315

Reaction notes

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