Ammonia → HCID 20279438, compound

HRID 1248357Notes

Reaction equation

HRID 1248357 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([C:6]1[C:16]([OH:17])=[CH:15][C:9]2[C:10]([C:12](Cl)=[O:13])=[CH:11][C:8]=2[CH:7]=1)=[O:5].[NH3:23]>ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([C:6]1[C:16]([OH:17])=[CH:15][C:9]2[C:10]([C:12]([NH2:23])=[O:13])=[CH:11][C:8]=2[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53714737HCID 53714737, compound

Product 1

HCID 20279438HCID 20279438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Over a period of 15 minutes, 4.86 g of 4-(2,6-dichlorobenzoyl)-5-hydroxybenzocyclobutene-1-carboxylic acid chloride are added dropwise, while stirring, to 15 ml of a 2.5 % solution of ammonia in dichloromethane. Stirring is carried out for 7 hours at room temperature, small amounts of a finely crystalline precipitate are filtered off and the filtrate is concentrated to dryness by evaporation, chromatographed over silica gel using dichloromethane/methanol (15:1) as eluant and recrystallised from ether/hexane. 4-(2,6-dichlorobenzoyl)-5-hydroxybenzocyclobutene-1-carboxamide is obtained having a melting point of 174°.

Workup

  1. waitis carried out for 7 hours at room temperature
  2. filtrationsmall amounts of a finely crystalline precipitate are filtered off
  3. concentrationthe filtrate is concentrated to dryness by evaporation
  4. customchromatographed over silica gel
  5. customrecrystallised from ether/hexane

Sources & evidence

ORD record
ord-f6df2521f012416f91009795bb03f36a
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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