3-Aminobenzyl alcohol → HCID 9923792, compound

HRID 1934932Notes

Reaction equation

HRID 1934932 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][OH:23].C(OC(O)C)C>N1C=CC=CC=1>[OH:23][CH2:22][C:21]1[CH:20]=[C:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 802933-Aminobenzyl alcoholHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 9923792HCID 9923792, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.0 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.98 g of 3-aminobenzyl alcohol, 0.32 ml of pyridine, and 12 ml of ethoxyethanol was stirred, under nitrogen, at reflux temperature for 3 h. The mixture was cooled and partitioned with dichloromethane and aqueous sodium bicarbonate. The organic layer was washed with water, dried and evaporated. The residue was washed with hot methanol to give 1.16 g of 4-[(3-(hydroxymethyl)phenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile as a solid, mp 250-255° C.

Workup

  1. temperatureat reflux temperature for 3 h
  2. temperatureThe mixture was cooled
  3. custompartitioned with dichloromethane and aqueous sodium bicarbonate
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. washThe residue was washed with hot methanol

Sources & evidence

ORD record
ord-d87756dfbb384767a3bf972d2e5ff089
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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