Dimethylformamide → HCID 19800031, compound

HRID 1646871Notes

Reaction equation

HRID 1646871 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C)([O-])C.[K+].CN(C=O)C>O>[N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[O:20][C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14209243HCID 14209243, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19800031HCID 19800031, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5.5 g of 3-bromo-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine, 2.2 g of potassium tert-butoxide and 50 ml of DMF was heated at 130° C. for 1 hour and then poured into 250 ml of water. The product was extracted with dichloromethane and ethyl acetate, dried and concentrated, and the residue was purifed by HPLC using dichloromethane:MeOH=95:5 as the eluent. The fractions containing the product were combined and concentrated. The residue was taken up in water and stirred for 1 hour, and the solid was filtered and recrystallized from toluene. The yield was 2.6 g, mp 164°-165° C.

Workup

  1. extractionThe product was extracted with dichloromethane and ethyl acetate
  2. customdried
  3. concentrationconcentrated
  4. additionThe fractions containing the product
  5. concentrationconcentrated
  6. filtrationthe solid was filtered
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-9e7f6e2fb44e4ca8aa676b47b60a3cfc
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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