4-Chlorobenzylamine → HCID 178427814, compound

HRID 2289921Notes

Reaction equation

HRID 2289921 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:18])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14]CC)=O)=[C:7]2[OH:17].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C(OCC)C>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:12]([C:8]2[CH:9]=[N:10][C:11]3[C:6]([C:7]=2[OH:17])=[CH:5][C:4]([CH3:18])=[CH:3][C:2]=3[F:1])=[O:14])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469646HCID 178469646, compound

Product 1

HCID 178427814HCID 178427814, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-fluoro-4-methylaniline (5.0 g) and diethyl ethoxymethylene-malonate (8.64 g) is heated to 130° C. for 2 h with removal of ethanol by a Dean-Stark trap. The mixture is cooled to 75° C. and diphenyl ether (50 mL) is added. The solution is heated to 250° C. for 2 h with removal of ethanol by a Dean-Stark trap, then cooled to room temperature. The resulting solid is collected, washed with hexanes and dried to yield 5.564 g of ethyl 8-fluoro-4-hydroxy-6-methylquinoline-3-carboxylate. A mixture of this ester (0.50 g) and 4-chlorobenzylamine (3.0 mL) are heated at 180° C. for 1 hour. The reaction is cooled and poured into 50 mL of diethyl ether. The resulting solid is filtered, dried, and purified by trituration in acetone to give the desired product (0.54 g).

Workup

  1. temperatureThe reaction is cooled
  2. filtrationThe resulting solid is filtered
  3. customdried
  4. custompurified by trituration in acetone

Sources & evidence

ORD record
ord-8d47212fb36249679fc8a285da54452c
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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