Ammonium Hydroxide → HCID 11085478, compound

HRID 726151Notes

Reaction equation

HRID 726151 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:12]\[C:13](Cl)=[O:14].[OH-].[NH4+:17]>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:12]\[C:13]([NH2:17])=[O:14]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 11107593HCID 11107593, compound

Product 1

HCID 11085478HCID 11085478, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (E)-2-(4-chloro-6-fluoro-1-indanylidene)acetyl chloride (4.0 g, 0.015 mol) [as prepared in example 1 g] in dichloromethane (36 ml) was added dropwise to an ice-cold mixture of 30% aqueous ammonium hydroxide (2.0 ml, 0.03 mol) and dichloromethane (100 ml) and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between 5% aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate solution was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel with ethyl acetate:hexanes (2:1) as eluent. Trituration of the resulting solid with pentane gave 1.47 g (43%) of (E)-2-(4-chloro-6-fluoro-1-indanylidene)acetamide as a white solid: m.p. 182°-184° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between 5% aqueous sodium bicarbonate and ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with ethyl acetate:hexanes (2:1) as eluent

Sources & evidence

ORD record
ord-eef055b58f5d4be49c45fc842f9b199a
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Reaction notes

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