Ammonium Hydroxide → HCID 23293655, compound

HRID 362870Notes

Reaction equation

HRID 362870 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:15])[CH2:7][CH:8]2[CH2:11][C:12](Cl)=[O:13])=[CH:4][CH:3]=1.[OH-].[NH4+:17]>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:15])[CH2:7][CH:8]2[CH2:11][C:12]([NH2:17])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23293646HCID 23293646, compound

Product 1

HCID 23293655HCID 23293655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(6-fluoro-3-oxo-1-indanyl)acetyl chloride (prepared from 0.024 mol of 2-(6-fluoro-3-oxo-1-indanyl)acetic acid) in dichloromethane (150 ml) was cooled to 0C and stirred rapidly while 50 ml of ammonium hydroxide, 28-30%, was added. The resulting mixture was allowed to warm to room temperature and stirring was continued for 18 hr. The volatiles from this mixture were removed by spin evaporation in vacuo and the residue was dissolved in dichloromethane (250 ml) and washed with water (3×50 ml). The dichloromethane phase was then slurried with Silica Gel 60 and the volatiles were removed by spin evaporation in vacuo. This silica was then applied to a column of Silica Gel 60 (51×400 mm) wet with dichloromethane and the product was removed by elution with methanol:dichloromethane (3:97) to give, after recrystallization from methanol, 2.4 g (48%) of 2-(6-fluoro-3-oxo-1-indanyl)acetamide as a yellow solid: m.p., 150°-152° C.;

Workup

  1. additionwas added
  2. customThe volatiles from this mixture were removed by spin evaporation in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane (250 ml)
  4. washwashed with water (3×50 ml)
  5. customthe volatiles were removed by spin evaporation in vacuo
  6. customthe product was removed by elution with methanol:dichloromethane (3:97)
  7. customto give
  8. customafter recrystallization from methanol, 2.4 g (48%) of 2-(6-fluoro-3-oxo-1-indanyl)acetamide as a yellow solid
  9. customm.p., 150°-152° C.

Sources & evidence

ORD record
ord-8de3642f0e374a26be45a1250307ca8b
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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