Hydrochloric Acid → Methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616169Notes

Reaction equation

HRID 1616169 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[CH2:12][N:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][C:17]([C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:19]=2)[C:14]1=[O:27])=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[CH2:12][N:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][C:17]([C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:19]=2)[C:14]1=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67281970Methyl 2-{3-[(tert-butoxycarbonyl)amino]benzyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67282939Methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-{3-[(tert-butoxycarbonyl)amino]benzyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.23 g, 0.57 mmol) in methylene chloride (5 mL) was added 4.0 M hydrochloric acid in 1,4-dioxane (7 mL, 28 mmol). The reaction mixture was stirred at rt for 2 h. The reaction mixture was concentrated to dryness to afford methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate.HCl (0.20 g, quant.). LC-MS: (FA) ES+ 309.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-acfdf69bf9574d76b8955b73d8955867
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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