Hydrochloric Acid → HCID 12668038, compound

HRID 2286391Notes

Reaction equation

HRID 2286391 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:9][CH2:8][C:7]2=[CH:10][C:11](=[O:22])[C:12](=[O:21])[C:13]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:6]2[CH2:5][CH2:4]1.Cl>CO>[Cl:1][C:10]1[C:7]2[CH2:8][CH2:9][N:3]([CH3:2])[CH2:4][CH2:5][C:6]=2[C:13]([S:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:12]([OH:21])[C:11]=1[OH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23462878HCID 23462878, compound

Product 1

HCID 12668038HCID 12668038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5 g. (0.0166 mole) of 7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine in 250 ml. of methanol was acidified with ethereal hydrogen chloride to yield the hydrochloride salt. The latter was dissolved in 300 ml. of methanol and 4.0 g. (0.0176 mole) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added portionwise under nitrogen and the mixture stirred at room temperature for 20 minutes. Ether was added to the reaction mixture and the solvents decanted to leave 3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione hydrochloride. This hydrochloride was dissolved in a minimum amount of methanol and then added to a methanolic hydrogen chloride solution, portionwise. The mixture was stirred at room temperature for 1 hour, the solvent was evaporated and the residue triturated with acetonitrile. The separated solid was purified via conversion to its free base to give 9-chloro-7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 173°-174° C.

Workup

  1. customthe solvent was evaporated
  2. customthe residue triturated with acetonitrile
  3. customThe separated solid was purified via conversion to its free base

Sources & evidence

ORD record
ord-127d921de5894b8f8c6fd1e32df95837
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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