Methanol → Methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Triethylamine	HCID 8471	—
Reactant	6-Bromoisoquinolin-1(2H)-one	HCID 15885182	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	Methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate	HCID 42609191	86%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a mixture of 6-bromo-2H-isoquinolin-1-one (4.00 g, 17.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (750 mg, 0.92 mmol), triethylamine (9.0 mL, 65 mmol) in a Parr bomb add a 1:1 mixture (v/v) of DMF and MeOH. Seal the apparatus and flush with 100 psi of carbon monoxide (3×). Heat the reaction mixture at 70° C. with stifling for 15 h. Remove the solvent in vacuo and wash the residue with MeOH then crystallize from dichloromethane to give 3.11 g of the desired product 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester as an off white solid in 86% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09079880B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-06bb70c7aa344f0bb48e5658da529e1b
Source note	uspto-grants-2015_07