Hydrochloric Acid → HCID 12773873, compound

HRID 1164541Notes

Reaction equation

HRID 1164541 reaction equation
[ClH:1].[CH3:2][N:3]1[C:7]([S:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:21])=[C:17]([OH:20])[CH:18]=3)[CH2:13][CH2:12][N:11]=2)=[N:6][N:5]=[N:4]1.[BH4-].[Na+].Cl>CO>[ClH:1].[CH3:2][N:3]1[C:7]([S:8][CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:21])=[C:17]([OH:20])[CH:18]=3)[CH2:13][CH2:12][NH:11]2)=[N:6][N:5]=[N:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 135755441HCID 135755441, compound

Product 1

HCID 12773873HCID 12773873, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(1-methyl-1H-tetrazol-5-yl)thiomethyl-6,7-dihydroxy-3,4-dihydroisoquinoline hydrochloride (0.2 g) was dissolved in methanol (5 ml) under warming. To the solution was added sodium borohydride (50 mg) and the mixture was stirred for 1.5 hours at room temperature. 10% Hydrochloric acid was added to the reaction mixture and the solution was concentrated. Dried methanol was added to the residue and the insoluble material was filtered off, after which the filtrate was evaporated. The residue was crystallized by treating with acetone to give 1-(1-methyl-1H-tetrazol-5-yl)thiomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.16 g), mp 215° to 216° C. (dec.).

Workup

  1. temperatureunder warming
  2. concentrationthe solution was concentrated
  3. additionDried methanol was added to the residue
  4. filtrationthe insoluble material was filtered off
  5. customafter which the filtrate was evaporated
  6. customThe residue was crystallized
  7. additionby treating with acetone

Sources & evidence

ORD record
ord-a1862f6027cc4b748fbf97955446639f
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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