Sodium Acetate → Methyl 5-acetoxy-1-cyclopropylisoquinoline-7-carboxylate

HRID 545208Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[C:4](=[CH:9][C:10]1[C:11]([CH:16]2[CH2:18][CH2:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:5][C:6]([OH:8])=O.[C:20]([O-])(=[O:22])[CH3:21].[Na+]>CC(O)=O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:10]2[C:15]([CH:14]=[CH:13][N:12]=[C:11]2[CH:16]2[CH2:18][CH2:17]2)=[C:6]([O:8][C:20](=[O:22])[CH3:21])[CH:5]=1)=[O:19]

Participants

Conditions

Temperature: 155 °C

Procedure

2-[1-(2-Cyclopropyl-pyridin-3-yl)-methylidene]-succinic acid 1-methyl ester (18.9 g, 72.4 mmol), sodium acetate (5.94 g, 72.4 mmol) was suspended in AcOH (150 ml) and heated at 155° C. for 6 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 6/4) to obtain the intended compound as a pale yellow solid.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated in vacuo
customThe residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 6/4)

Sources & evidence

ORD record: ord-023ecbd4f755405e8eaf1c417746a67f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935712B2

Reaction notes

Loading…