Hydrochloric Acid → Methyl 2-{3-[(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616160Notes

Reaction equation

HRID 1616160 reaction equation
C(OC([N:8]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[CH2:9][CH2:10][CH2:11][N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=2)[C:13]1=[O:26])=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=3)[C:13]2=[O:26])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67281624Methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67282386Methyl 2-{3-[(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylateYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (71 mg, 0.15 mmol) in methylene chloride (2 mL) was added 4.0 M hydrochloric acid in 1,4-dioxane (2.0 mL, 8.0 mmol). The reaction mixture was stirred at rt for 1 d. The mixture was then concentrated to dryness to afford methyl 2-{3-[(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (56 mg, quant.). LC-MS: (FA) ES+ 367.

Workup

  1. concentrationThe mixture was then concentrated to dryness

Sources & evidence

ORD record
ord-802199b79aab4dc9b31c765e371880c2
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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