Acetic Anhydride → 5-Acetylamino-2-n-propylpyridine

HRID 1422123Notes

Reaction equation

HRID 1422123 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(O)(=O)C>[C:11]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 138607306-Propylpyridin-3-amine

Product 1

HCID 187069935-Acetylamino-2-n-propylpyridineYield 80.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-amino-2-n-propylpyridine (example 23, step2) (62.7 g, 0.46 mol) and 45.7 g (0.483 mol) of acetic anhydride in 50 ml of acetic acid was refluxed for 3 hours in a nitrogen atmosphere. The mixture was evaporated and the oily residue was made slightly alkaline (pH=9.2) with a 10% sodium hydroxide solution. The precipitate was filtered off, and triturated with a mixture of water (1000 ml) and heptane (500 ml). The precipitate was filtered off, dried and resuspended in 400 ml of heptane. The resulting precipitate was filtered off and dried to yield 65.7 g (80%) of 5-acetylamino-2-n-propylpyridine. M.p. 122-24° C. 1H-NMR (CDCl3, 200 MHz) δ: 0.95 (t, 3H), 1.72 (sext, 2H), 2.20 (s, 3H), 2.73 (t, 2H), 7.10 (d, 1H), 7.70 (br s, 1H), 8.09 (dd, 1H), 8.43 (d, 1H).

Workup

  1. temperaturewas refluxed for 3 hours in a nitrogen atmosphere
  2. customThe mixture was evaporated
  3. filtrationThe precipitate was filtered off
  4. customtriturated with a mixture of water (1000 ml) and heptane (500 ml)
  5. filtrationThe precipitate was filtered off
  6. customdried
  7. filtrationThe resulting precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-13ea72d6495e4a80b1193c4393423228
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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