4-Chlorobenzylamine → HCID 178426083, compound

HRID 2290015Notes

Reaction equation

HRID 2290015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([O:15]CC)=O)=[C:5]2[OH:18].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([NH:25][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Cl:19])=[CH:21][CH:22]=1)=[O:15])=[C:5]2[OH:18]

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469535HCID 178469535, compound

Product 1

HCID 178426083HCID 178426083, compound

Conditions

Temperature
190 °C

Procedure

A mixture of 3.0 g of ethyl 6-chloro-4-hydroxy-8-methyl-3-quinolinecarboxylate (Maybridge Chemical Co.) and 7.0 mL of 4-chlorobenzylamine is stirred 3 h at 190° C. The mixture is cooled to 25° C. and is diluted with 35 mL of hexanes. The precipitate is collected by filtration and washed with 10 mL of hexanes. It is dried in a stream of air and then it was recrystallized from 30 mL of glacial acetic acid. It was dried at 20 torr and 100° C. for 20 h. The yield is 1.6 g (40%).

Workup

  1. temperatureThe mixture is cooled to 25° C.
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with 10 mL of hexanes
  4. customIt is dried in a stream of air
  5. customit was recrystallized from 30 mL of glacial acetic acid
  6. customIt was dried at 20 torr and 100° C. for 20 h

Sources & evidence

ORD record
ord-44b6c2ba1cd648ad98b0a8a45db91bce
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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