3-Chloroaniline → HCID 54693832, compound

HRID 2292002Notes

Reaction equation

HRID 2292002 reaction equation
[OH:1][C:2]1[C:3]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9]C)=O.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>CCOCC>[OH:1][C:2]1[C:3]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:17]([Cl:16])[CH:18]=1)=[O:9]

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 54693830Benzo[b]thiophene-2-carboxylic acid, 5-chloro-3-hydroxy-, methyl ester

Product 1

HCID 54693832HCID 54693832, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of methyl 3-hydroxy-5-chlorobenzo[b]thiophene-2-carboxylate (1.21 g; 0.005M) and 3-chloroaniline (1.28 g; 0.010M) is heated under a nitrogen atmosphere at 170° C. for 90 minutes. The reaction mixture was cooled to room temperature, taken up in 10 ml of ether, collected the solid, washed with 10 ml of ether, air dried, and recrystallized from ethyl acetate to give 0.95 g (56% yield) of the title compound as a light grey solid, m.p. 233°-235° C. (dec).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customcollected the solid
  3. washwashed with 10 ml of ether, air
  4. customdried
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b41c64df5a5e415e8d837b155dc8cf6d
Source dataset
uspto-grants-1989_01
Patent number
US04800211

Reaction notes

Loading…