Hydrochloric Acid → Methyl 6-aminoquinoline-3-carboxylate dihydrochloride

HRID 1894957Notes

Reaction equation

HRID 1894957 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:12]2)=O)(C)(C)C.[ClH:23].O1CCOCC1>C(Cl)Cl>[ClH:23].[ClH:23].[NH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:12]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67002181Methyl 6-(tert-butoxycarbonylamino)quinoline-3-carboxylate

Product 1

HCID 67002244Methyl 6-aminoquinoline-3-carboxylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-[(tert-butoxycarbonyl)amino]quinoline-3-carboxylate (Int-2, 1.28 g, 4.23 mmol) in methylene chloride (38 mL) was added hydrochloric acid in 1,4-dioxane (4.0 M, 10.6 mL, 42.3 mmol). The reaction was stirred at room temperature overnight then concentrated under reduced pressure. The crude reside was dried in vacuo and used as obtained. LC-MS: (FA) ES+ 203; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.14 (s, 1H), 9.08 (d, J=1.8 Hz, 1H), 8.10 (d, J=9.1 Hz, 1H), 7.62 (dd, J=9.1, 2.4 Hz, 1H), 7.33 (d, J=1.7 Hz, 1H), 3.96 (s, 9H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe crude reside was dried in vacuo
  3. customas obtained

Sources & evidence

ORD record
ord-1d17512a48954b0083454f4a875fba2c
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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