Succinic anhydride → Butanoic acid, 4-(nonylamino)-4-oxo-

HRID 1788882Notes

Reaction equation

HRID 1788882 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([NH2:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CC(C)=O>[CH2:8]([NH:17][C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 16215Nonylamine

Product 1

HCID 454082Butanoic acid, 4-(nonylamino)-4-oxo-Yield 79.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of succinic anhydride (25.0 g, 0.25 mol) in 150 mL acetone was added dropwise 35.8 g (0.25 mol) of nonylamine. The addition of the amine required 15 minutes, with the acetone solution reaching reflux before the addition was complete. Five minutes after the end of addition, a precipitate formed and the reaction mixture quickly became thick with suspended solids. Following addition of the amine the reaction mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration and washed with cold acetone. Air drying afforded 48.5 g of 4-nonylamino-4-oxobutyric acid as white, fluffy crystals, mp 114°-115.5° C. Upon standing the filtrate deposited crystals which were collected by filtration, washed with cold acetone, and air dried to yield an additional 10.9 g of the acid, mp 114°-115.5° C. Total yield was 59.4 g (98% of theoretical).

Workup

  1. additionFive minutes after the end of addition
  2. customa precipitate formed
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with cold acetone
  5. customAir drying

Sources & evidence

ORD record
ord-8a125ea60f50441aa95a30af6dfecf36
Source dataset
uspto-grants-1987_08
Patent number
US04686063

Reaction notes

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