Methanol → HCID 50991573, compound

HRID 716943Notes

Reaction equation

HRID 716943 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:13][C:14]3[C:19]([N:20]=2)=[CH:18][C:17]([C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=3)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CO.ClCCl.[OH-].[Na+]>O>[C:1]([NH:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:13][C:14]3[C:19]([N:20]=2)=[CH:18][C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=3)[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67041990HCID 67041990, compound

Product 1

HCID 50991573HCID 50991573, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100-mL round-bottom flask was placed methyl 3-(4-acetamidopiperidin-1-yl)-2-phenylquinoxaline-6-carboxylate (100 mg, 0.25 mmol, 1.00 equiv), methanol (15 mL), dichloromethane (7 mL). To this was added a solution of sodium hydroxide (1.5 g, 37.50 mmol, 151.50 equiv) in water (7 mL). The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum and diluted with 10 ml of H2O. The pH of the aqueous solution was adjusted to 3 with hydrochloric acid. The resulting solids were collected by filtration. This resulted in 95 mg (94%) of 3-(4-acetamidopiperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a light yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additiondiluted with 10 ml of H2O
  4. filtrationThe resulting solids were collected by filtration
  5. customThis resulted in 95 mg (94%) of 3-(4-acetamidopiperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a light yellow solid

Sources & evidence

ORD record
ord-00b8818feba94446b45cae46524bcb18
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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