Hydrochloric Acid → Trans-2-carboxy-5,7-dichloro-4-(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

HRID 484445Notes

Reaction equation

HRID 484445 reaction equation
[C:1]([C@H:4]1[CH2:13][C@H:12]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:24]C(OC(C)(C)C)=O)[CH:18]=2)=[O:16])[C:11]2[C:6](=[CH:7][C:8]([Cl:33])=[CH:9][C:10]=2[Cl:32])[NH:5]1)([OH:3])=[O:2].Cl>C(OCC)(=O)C>[ClH:32].[C:1]([C@H:4]1[CH2:13][C@H:12]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH2:24])[CH:18]=2)=[O:16])[C:11]2[C:6](=[CH:7][C:8]([Cl:33])=[CH:9][C:10]=2[Cl:32])[NH:5]1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67691019Trans-2-carboxy-5,7-dichloro-4-(3-tert-butyloxycarbonylaminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline

Product 1

HCID 67690807Trans-2-carboxy-5,7-dichloro-4-(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochlorideYield 124.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of trans-2-carboxy-5,7-dichloro-4-(3-tert-butyloxycarbonylaminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline (85 mg) in ethyl acetate (20 ml) was added 25 ml of ethyl acetate saturated with hydrogen chloride gas and the mixture was stirred in a stoppered flask for 6 h. The ethyl acetate and excess hydrogen chloride were removed in vacuo and the solid residue was recrystallised from ethyl acetate/methanol to give the title compound as colourless crystals (46 mg), m.p. 199°-200° C. δ (DMSO, 360 MHz) 1.76 (1H, ddd, J=13.2, 13.1 and 3.9 Hz, CHACHBHCCHD), 2.26 (1H, dm J=13.2 Hz, CHACHBHCCHD), 3.96-4.06 (3H, m, ArCH2NH2 and CHACHBHCCHD), 5.29 (1H, m, CHACHBHCCHD), 6.66 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.85 (1H, s, NH), 6.92 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.48 (1H, t, J=7.8 Hz, Ar-H), 7.63 (1H, d, J=7.8 Hz, Ar-H), 7.88 (1H, d, J=7.8 Hz, Ar-H), 8.03 (1H, s, Ar-H), 8.38 (1H, br s, NH2), 8.72 (1H, d, J=7 Hz, NHCO); m/e (FAB+), 394 (M+1), 93 (100%).

Workup

  1. customThe ethyl acetate and excess hydrogen chloride were removed in vacuo
  2. customthe solid residue was recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-dc1e71a06c804199a514bb036d038ad1
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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