Ammonium Hydroxide → HCID 15491029, compound

HRID 362855Notes

Reaction equation

HRID 362855 reaction equation
[OH-].[NH4+:2].[F:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:18])([CH3:17])[CH2:9]/[C:10]/2=[CH:13]\[C:14](Cl)=[O:15])=[CH:6][CH:5]=1>ClCCl>[F:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:18])([CH3:17])[CH2:9]/[C:10]/2=[CH:13]\[C:14]([NH2:2])=[O:15])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23293589HCID 23293589, compound

Product 1

HCID 15491029HCID 15491029, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 30% aqueous ammonium hydroxide (10 ml, 76 mmol, Mallinckrodt) was added to the solution of (E)-2-(6-fluoro-3,3-dimethyl-1-indanylidene)acetyl chloride (0.01363 mol) obtained from Example 41h diluted with dichloromethane (200 ml) and cooled to 0° C. The biphasic solution was stirred rapidly and allowed to warm to room temperature over 18 h. The reaction solution was concentrated by spin evaporation in vacuo, diluted with dichloromethane (200 ml), and washed with IN aqueous hydrochloric acid (McIntosh), a solution of 5% aqueous sodium bicarbonate (Mallinckrodt), dried with magnesium sulfate (Mallinckrodt), and concentrated by spin evaporation in vacuo. The residue was chromatographed on Silica Gel 60 using ethyl acetate-hexanes (1:1), and then ethyl acetate. Fractions containing (E)-2-(6-fluoro-3,3-dimethyl-1-indanylidene) acetamide were combined and concentrated by spin evaporation in vacuo. Recrystallization from dichloromethane-hexanes gave 2.85 g (95%) of (E)-2-(6fluoro-3,3-dimethyl-1-indanylidene)acetamide as a white crystalline solid, m.p., 167°-168° C.;

Workup

  1. temperatureto warm to room temperature over 18 h
  2. concentrationThe reaction solution was concentrated by spin evaporation in vacuo
  3. additiondiluted with dichloromethane (200 ml)
  4. washwashed with IN aqueous hydrochloric acid (McIntosh)
  5. dry with materiala solution of 5% aqueous sodium bicarbonate (Mallinckrodt), dried with magnesium sulfate (Mallinckrodt)
  6. concentrationconcentrated by spin evaporation in vacuo
  7. customThe residue was chromatographed on Silica Gel 60 using ethyl acetate-hexanes (1:1)
  8. additionFractions containing (E)-2-(6-fluoro-3,3-dimethyl-1-indanylidene) acetamide
  9. concentrationconcentrated by spin evaporation in vacuo
  10. customRecrystallization from dichloromethane-hexanes

Sources & evidence

ORD record
ord-5b5566eddc7947c39714ee85536994ac
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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