Dimethylformamide → HCID 14209220, compound

HRID 1646865Notes

Reaction equation

HRID 1646865 reaction equation
Br[C:2]1[C:3]([CH3:16])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C)([O-])C.[K+].CN(C)C=O>O>[CH3:16][C:3]1[C:2]2[O:15][CH2:14][CH2:13][NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14209235HCID 14209235, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14209220HCID 14209220, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-N-(2-hydroxyethyl)-2-methyl-4-quinolinamine (11.5 g), potassium-tert-butoxide (3.7 g) and 100 ml of dimethylformamide (DMF) was stirred at 80° C. for 3 hours. The mixture was cooled and diluted with 600 ml of water and thereafter kept in a refrigerator for 2 days. The resultant solid was filtered and recrystallized from isopropanol. The yield was 3.3 g, mp 203°-204° C.

Workup

  1. temperatureThe mixture was cooled
  2. waitkept in a refrigerator for 2 days
  3. filtrationThe resultant solid was filtered
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-eb2c3596f636419c893299d0fdaf72f4
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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