Selenium Dioxide → HCID 21034922, compound

HRID 1833116Notes

Reaction equation

HRID 1833116 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2].C[O:30]C1C=C2C(=CC=1OC)C(C(=O)C1C=CC=C(OC)C=1)=NC=C2CC(O)=O.[Se](=O)=O>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([C:20](=[O:30])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 11428969HCID 11428969, compoundHCID 21034909HCID 21034909, compound

Product 1

HCID 21034922HCID 21034922, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3-methoxybenzyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester (159 mg, 0.417 mmol, the intermediate in the preparation of [6,7-Dimethoxy-1-(3-methoxy-benzoyl)-isoquinolin-4-yl]-acetic acid) (Example 7) was dissolved into 4 ml of acetic acid. Then selenium dioxide (69.5 mg, 1.50 eq) was added. The mixture was refluxed for 20 minutes and then evaporated to dryness. The residue was suspended into ethyl acetate and the mixture was passed through a layer of silica gel. The filtrate was evaporated to give 1-(3-methoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester as a solid (135 mg, 82%). This material (95.6 mg, 0.242 mmol) was suspended into 5 ml of methanol. Then 1N sodium hydroxide solution (0.5 ml) was added. The mixture was refluxed for 1 hr. TLS showed complete disappearance of the starting material. The mixture was evaporated and the residue was dissolved into 5 ml of water and then filtered. The filtrate was acidified with 1N hydrochloric acid to give 6,7-Dimethoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carboxylic acid as a solid (76 mg, 86%). ES-MS calculated for C20H17NO6 (m/e) 367.36, observed 368.4 (M+1). 1H-NMR is consistent with the desired structure.

Workup

  1. temperatureThe mixture was refluxed for 20 minutes
  2. customevaporated to dryness
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c10804f3695f44359b0138a9f154da97
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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