Ammonium Hydroxide → Glutarimide, 3-methyl-3-propyl-

HRID 905170Notes

Reaction equation

HRID 905170 reaction equation
[CH3:1][C:2]([CH2:11][CH2:12][CH3:13])([CH2:7][C:8](O)=[O:9])[CH2:3][C:4](O)=[O:5].[NH4+:14].[OH-]>>[CH3:1][C:2]1([CH2:11][CH2:12][CH3:13])[CH2:7][C:8](=[O:9])[NH:14][C:4](=[O:5])[CH2:3]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 129374233-Methyl-3-n-propylglutaric Acid

Product 1

HCID 95853Glutarimide, 3-methyl-3-propyl-Yield 80%

Procedure

A 10 g (0.06 mole) quantity of the anhydride prepared in Example 1 was added in small portions to 120 mL conc. NH4OH. After the addition was completed, the mixture was heated to a gentle reflux and stirred for 4 hr. Upon cooling the reaction mixture, a yellow oil precipitated which solidified to a glass. Crystallization of the glass from isopropyl alcohol gave 8 g (80%) of crude product, m.p. 110°-120° C. (literature m.p. 115°-116°, Cf: N. S. Benica and C. O. Wilson, J. Am. Pharm. Assoc., 39, page 451-454 (1950)).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated to
  3. temperaturea gentle reflux
  4. temperatureUpon cooling the reaction mixture
  5. customa yellow oil precipitated which
  6. customCrystallization of the glass from isopropyl alcohol

Sources & evidence

ORD record
ord-b8f20aecd927469c8db006dbd13704ac
Source dataset
uspto-grants-1983_12
Patent number
US04423049

Reaction notes

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