Lithium Hydroxide → HCID 86712025, compound

HRID 1051384Notes

Reaction equation

HRID 1051384 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[Li+].[OH-]>C1COCC1.O>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86712026HCID 86712026, compound

Product 1

HCID 86712025HCID 86712025, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 96 (132 mg, 0.45 mmol) in THF (2.19 mL) and water (0.324 mL) was treated with solid LiOH (24 mg, 0.99 mmol) and stirred for 3 h. THF was removed in vacuo, and the mixture was suspended in water (6.0 mL) and treated with aqueous HCl (10 M, 0.27 mL). A yellow-brown precipitate was collected by vacuum filtration to afford 3-(2-methylpyridin-4-ylamino)isoquinoline-6-carboxylic acid (98) as a yellow solid, which was used in subsequent steps without further purification.

Workup

  1. customTHF was removed in vacuo
  2. additiontreated with aqueous HCl (10 M, 0.27 mL)
  3. filtrationA yellow-brown precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-2ed0918bacde445f927be015be878181
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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