4-Chlorobenzylamine → HCID 178522889, compound

HRID 2289923Notes

Reaction equation

HRID 2289923 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C(OCC)C>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:13]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=3)=[O:15])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469614HCID 178469614, compound

Product 1

HCID 178522889HCID 178522889, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

3-Iodoaniline (8.50 mL) and diethyl ethoxymethylenemalonate (14.30 mL) are heated at 130° C. for 1 hour. The reaction is cooled to room temperature and 70 mL diphenyl ether is added. The solution is heated at 250° C. for 1.5 hours with removal of ethanol by a Dean-Stark trap. The reaction is cooled to room temperature and the resulting solid filtered, washed with hexanes, and dried. The solid is triturated in ethyl acetate to give 12.82 g of ethyl 4-hydroxy-7-iodoquinoline-3-carboxylate. A mixture of this ester (0.35 g) and 4-chlorobenzylamine (3.0 mL) are heated at 180° C. for 1 hour. The reaction is cooled to 70° C. and poured into 50 mL diethyl ether. A tan solid which crystallizes slowly out of diethyl ether is obtained. The solid is recrystallized from ethyl acetate/hexanes to give the desired product (0.22 g).

Workup

  1. temperatureThe reaction is cooled to 70° C.
  2. customA tan solid which crystallizes slowly out of diethyl ether
  3. customis obtained
  4. customThe solid is recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-acaeadf94f6b478e83ccf0d9a419d885
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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