Sodium Hydroxide → HCID 57520190, compound

HRID 1520157Notes

Reaction equation

HRID 1520157 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[C:27]4[C:22](=[CH:23][C:24]([C:28]([N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[O:29])=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:36]([O:38]C)=[O:37])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([N:18]3[C:27]4[C:22](=[CH:23][C:24]([C:28]([N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[O:29])=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:36]([OH:38])=[O:37])[CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68194235HCID 68194235, compound

Product 1

HCID 57520190HCID 57520190, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-[6-[(morpholin-4-yl)carbonyl]-1,2,3,4-tetrahydroquinolin-1-yl]quinoxaline-6-carboxylate (107 mg, 0.20 mmol) in methanol (30 ml) and water (2.0 ml) was added sodium hydroxide (32 mg, 0.8 mmol) with stifling overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (20 ml) and adjusted to pH 4 with hydrogen chloride (3 N). The solids were collected by filtration to afford 2-(4-fluorophenyl)-3-[6-[(morpholin-4-yl)carbonyl]-1,2,3,4-tetrahydroquinolin-1-yl]quinoxaline-6-carboxylic acid as a light yellow solid (90 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (20 ml)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-c1a8eaa835184bf1a105e3fa09983a90
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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