Acetic Anhydride → HCID 20039927, compound

HRID 1762880Notes

Reaction equation

HRID 1762880 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[CH:4][CH:3]=1.[C:18]([O-])(=[O:20])[CH3:19].[Na+].C(OC(=O)C)(=O)C.C(=O)(O)[O-].[K+]>O.C(O)C.C(OCC)(=O)C>[C:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[CH:6][CH:7]=1)(=[O:20])[CH3:19]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 516893Potassium BicarbonateHCID 517045Sodium AcetateHCID 20039934HCID 20039934, compound

Product 1

HCID 20039927HCID 20039927, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4 g (0.017 mol) of 7-[(4-hydroxyphenyl)methylamino]heptanenitrile and 2.1 g (0.026 mol) anhydrous sodium acetate in 14 mL (0.17 mol) of acetic anhydride was stirred under nitrogen at room temperature. After 11/2 hours 15 mL of ethyl acetate was added followed by 49 mL of absolute ethanol. The reaction was stirred 18 hours at room temperature, cooled, and 61 mL of water was added followed by about 11 g of solid potassium bicarbonate. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed three times with saturated sodium bicarbonate solution, two times with saturated sodium chloride solution, and dried over magnesium sulfate. The solution was concentrated in vacuo to 3.4 gm of amber oil which was distilled at 170°-172°/0.08 mm in a Kugelrohr to yield 2.7 g (59%) of 7-[[4-(acetyloxy)phenyl]methylamino]heptanenitrile.

Workup

  1. temperaturecooled
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. washwashed three times with saturated sodium bicarbonate solution, two times with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo to 3.4 gm of amber oil which
  7. distillationwas distilled at 170°-172°/0.08 mm in a Kugelrohr

Sources & evidence

ORD record
ord-91172968d81d48c58d7fd2d8b3431beb
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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