Hydrochloric Acid → HCID 67081846, compound

HRID 1666306Notes

Reaction equation

HRID 1666306 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[CH:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[C:9]2[C:4](=[CH:5][C:6]([O:25][CH3:26])=[CH:7][CH:8]=2)[CH2:3]1.[ClH:27]>>[ClH:27].[NH2:1][N:2]1[C:11](=[O:12])[CH:10]([C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)[C:9]2[C:4](=[CH:5][C:6]([O:25][CH3:26])=[CH:7][CH:8]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67081847HCID 67081847, compound

Product 1

HCID 67081846HCID 67081846, compound

Procedure

The acetamide (1.4 g) from step 3 above was dissolved in trifluoroacetic acid (15 ml) and the solution was kept at 40° C. for 5 hours. The reaction mixture was concentrated to dryness, and the residue partitioned between aqueous hydrochloric acid (50 ml, 2 M) and ethyl acetate (50 ml). The aqueous phase was made alkaline with sodium hydroxide and extracted with dichloromethane (2×50 ml). The organic phase was dried and concentrated to dryness, giving the title compound as pale yellow solid (0.97 g). The amine was converted to the hydrochloride, which was crystallized from methanol, giving 2-amino-4-(3,4,5-trimethoxyphenyl)-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone hydrochloride, m.p. 164-167° C.

Workup

  1. customwas crystallized from methanol

Sources & evidence

ORD record
ord-2de9487a9ab44f56b27f92bed8e35faf
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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