Hydrochloric Acid → HCID 178428133, compound

HRID 49202Notes

Reaction equation

HRID 49202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:20][NH:21][C:22]([NH2:24])=[NH:23])[CH2:10]1.Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:20][NH:21][C:22]([NH2:24])=[NH:23])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178428132HCID 178428132, compound

Product 1

HCID 178428133HCID 178428133, compoundYield 196%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (−)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (1.2 g) in ethanol (20 ml) was combined with concentrated hydrochloric acid (0.76 ml) and concentrated. The resultant crystal was recrystallized from a solvent mixture of ethanol and water to obtain (−)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound J) (1.3 g, 99.4% ee). (This compound was proven to have an absolute configuration of an S form based in an X-ray crystal structure analysis.)

Workup

  1. concentrationconcentrated
  2. customThe resultant crystal was recrystallized from a solvent mixture of ethanol and water

Sources & evidence

ORD record
ord-0f55b4e3c5c84aca853d6d4e1f0a4eaa
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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