Ammonia → HCID 13210723, compound

HRID 1979709Notes

Reaction equation

HRID 1979709 reaction equation
[N+]([O-])(O)=O.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][N:16]([CH3:18])[CH2:15][C:14]3[S:19][CH:20]=[CH:21][C:13]2=3)=[CH:8][CH:7]=1.[NH3:22].F[C:24](F)(F)[C:25]([OH:27])=O>>[C:25]([NH:22][C:20]1[S:19][C:14]2[CH2:15][N:16]([CH3:18])[CH2:17][CH:12]([C:9]3[CH:8]=[CH:7][C:6]([Br:5])=[CH:11][CH:10]=3)[C:13]=2[CH:21]=1)(=[O:27])[CH3:24]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric Acid2×HCID 6422Trifluoroacetic acidHCID 132107214-(4-Bromophenyl)-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 13210723HCID 13210723, compound

Procedure

25 ml of fuming nitric acid were added dropwise to 14.5 gm (0.047 mol) of 4-(p-bromo-phenyl)-6-methyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine in 100 ml of trifluoroacetic acid, while cooling, so that the temperature did not exceed 20° C. After all the nitric acid had been added, the mixture was stirred for a further 30 minutes. The reaction mixture was then poured over ice, concentrated ammonia was added until the mixture reacted alkaline, and the mixture was then extracted with methylene chloride. After the solvent had been evaporated, the residual 4-(p-bromo-phenyl)-6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[2,3-c]pyridine was crystallized as its hydrochloride from alcoholic hydrochloric acid.

Workup

  1. temperaturewhile cooling, so that the temperature
  2. customdid not exceed 20° C
  3. additionwas added until the mixture
  4. customreacted alkaline
  5. extractionthe mixture was then extracted with methylene chloride
  6. customAfter the solvent had been evaporated
  7. customthe residual 4-(p-bromo-phenyl)-6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[2,3-c]pyridine was crystallized as its hydrochloride from alcoholic hydrochloric acid

Sources & evidence

ORD record
ord-5b6fb188493b4ccf95d6da404b1fbecf
Source dataset
uspto-grants-1984_11
Patent number
US04482559

Reaction notes

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