Hydrochloric Acid → HCID 86712406, compound

HRID 2174207Notes

Reaction equation

HRID 2174207 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=[CH:3][C:2]=1[OH:11].[H-].[Na+].[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[CH:17]=[O:18].Cl>CN(C)C=O>[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([O:11][C:2]2[CH:3]=[N:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[N:1]=2)[C:16]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 678472-Chloro-6-fluorobenzaldehydeHCID 178516734HCID 178516734, compound

Product 1

HCID 86712406HCID 86712406, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.3 g of 5,6,7,8-tetrahydroquinoxalin-2-ol were dissolved in 5 ml of dimethylformamide. 0.1 g of sodium hydride were added thereto. 0.35 g of 2-chloro-6-fluoro-benzaldehyde were added to the reaction solution followed by stirring for 3 hours at 100° C. 1 N hydrochloric acid was then added to the reaction solution. Subsequently, the reaction solution was extracted with ethyl acetate and the organic layer was concentrated followed by purifying by silica gel column chromatography to obtain 0.26 g of 2-chloro-6-(5,6,7,8-tetrahydro-quinoxalin-2-yloxy)-benzaldehyde.

Workup

  1. extractionSubsequently, the reaction solution was extracted with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. customby purifying by silica gel column chromatography

Sources & evidence

ORD record
ord-c7cc612b6f954265bcc8c96f1cba8df4
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

Loading…