Sodium Hydroxide → 3-(1H-Indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 716997Notes

Reaction equation

HRID 716997 reaction equation
[N:1]1([C:10]2[C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][C:16]([C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=3)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+]>CO.O>[N:1]1([C:10]2[C:11]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67042171Methyl 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 509912123-(1H-Indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylate (40 mg, 0.11 mmol, 1.00 equiv) in methanol (10 mL). A solution of sodium hydroxide (21.1 mg, 0.53 mmol, 5.00 equiv) in H2O (2 mL) was added. The resulting solution was stirred for 2 hrs at 50° C. in an oil bath. The resulting mixture was concentrated in vacuo. The resulting solution was diluted with 20 mL of H2O. The pH value of the aqueous solution was adjusted to 4-5 with aq. 1N hydrogen chloride. The resulting solids were collected by filtration. The crude product (50 mL) was further purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, silica gel; mobile phase, H2O/CH3CN=100:1 increasing to H2O/CH3CN=100:60 within 40 min; Detector, UV 254 nm. This resulted in 15 mg (38%) of 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. additionThe resulting solution was diluted with 20 mL of H2O
  4. filtrationThe resulting solids were collected by filtration
  5. customThe crude product (50 mL) was further purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1)
  6. waitmobile phase, H2O/CH3CN=100:1 increasing to H2O/CH3CN=100:60 within 40 min
  7. customThis resulted in 15 mg (38%) of 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-af0d67e992d24c3590862153df4db17f
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

Loading…