Lithium Hydroxide → HCID 11350419, compound

HRID 1833111Notes

Reaction equation

HRID 1833111 reaction equation
C([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:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]([OH:31])=[O:30])[CH:22]=2)=[N:8][CH:7]=1)=[O:5])C.[OH-].[Li+]>CO>[C:29]([CH2:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:20]([C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=1)=[O:32])([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21034870HCID 21034870, compound

Product 1

HCID 11350419HCID 11350419, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-carboxymethoxybenzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (89 mg, 0.19 mmol) in 5 ml of methanol was added lithium hydroxide solution (0.5 N, 1.0 ml). The mixture was stirred at room temperature overnight. The reaction mixture was loaded to a preparative HPLC for purification to give 1-(3-Carboxymethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid as a fluffy solid (72.6 mg, 92%). ES-MS calcd for C21H17NO8 (m/e) 411.4, obsd 412.3 (M+H).

Workup

  1. customThe reaction mixture was loaded to a preparative HPLC for purification

Sources & evidence

ORD record
ord-d63507a28afc441190b92a7bb4d7cfc2
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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