Dimethylformamide → HCID 19800031, compound

HRID 1252417Notes

Reaction equation

HRID 1252417 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 purified 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. customthe residue was purified by HPLC
  5. additionThe fractions containing the product
  6. concentrationconcentrated
  7. filtrationthe solid was filtered
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-b5414ddf5a2343b081d3026e5e10cc4e
Source dataset
uspto-grants-1988_05
Patent number
US04743601

Reaction notes

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