Water → HCID 14209225, compound

HRID 1646870Notes

Reaction equation

HRID 1646870 reaction equation
[H-].[Na+].Br[C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.O>CN(C=O)C>[C:17]1([CH:16]2[O:23][C:4]3[CH:5]=[N:6][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]=3[NH:14][CH2:15]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 14209242HCID 14209242, compound

Product 1

HCID 14209225HCID 14209225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydride (obtained from 2 g of 50% suspension in mineral oil) was added to a solution of 3-bromo-N-(2-hydroxy-2-phenylethyl)-4-quinolinamine (10 g) in 50 ml of DMF and the mixture was stirred at 90° C. for two hours. After cooling to room temperature, it was poured into 250 ml of water and the product extracted with two portions of 100 ml dichloromethane. The dichloromethane layer was dried over sodium sulfate and concentrated. The oily residue was dissolved in 80 ml of isopropanol, the solution was poured into 250 ml of ice water and the mixture was stirred for 1 hour. The solid was filtered and recrystallized from isopropanol. The yield was 3.1 g, mp 194°-195° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe product extracted with two portions of 100 ml dichloromethane
  3. dry with materialThe dichloromethane layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe oily residue was dissolved in 80 ml of isopropanol
  6. additionthe solution was poured into 250 ml of ice water
  7. stirringthe mixture was stirred for 1 hour
  8. filtrationThe solid was filtered
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-fae6bdc58de34b6e93bfa58d7808cf9f
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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