Methyl 2-acetamidoacrylate → Methyl 7-chloroisoquinoline-3-carboxylate

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=O.C([NH:14][C:15](=[CH2:20])[C:16]([O:18][CH3:19])=[O:17])(=O)C>>[Cl:10][C:7]1[CH:6]=[C:3]2[C:2]([CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[N:14]=[CH:4]2)=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 98644Methyl 2-acetamidoacrylate

HCID 153912792-Bromo-5-chlorobenzaldehyde

Product 1

HCID 17842489Methyl 7-chloroisoquinoline-3-carboxylateYield 25%

Procedure

methyl 7-chloro-isoquinoline-3-carboxylate was prepared using the procedure described in example 12A: 2-bromo-5-chlorobenzaldehyde was reacted with methyl 2-acetamidoacrylate at 110° C. for 24 hours to yield methyl 7-chloro-isoquinoline-3-carboxylate (25%) as brown solid.

Workup

custommethyl 7-chloro-isoquinoline-3-carboxylate was prepared

Sources & evidence

ORD record: ord-ffda6479c38f4da3a4e42b85c693c17d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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