Acetic Anhydride → HCID 22141583, compound

HRID 1826246Notes

Reaction equation

HRID 1826246 reaction equation
[C:1]1([P:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl.CN(C1C=CN=CC=1)C>[C:15]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[N:13]=[C:12]([NH:14][C:28](=[O:30])[CH3:29])[CH:11]=[CH:10][CH:9]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 221415846-(Diphenylphosphanyl)pyridin-2-amine

Product 1

HCID 22141583HCID 22141583, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.10 g (0.36 mmol) of 6-(diphenylphosphino)-2-aminopyridine from example 14.3.1 was dissolved in 2.0 ml of dichloromethane and admixed with 0.05 ml (0.04 g, 0.40 mmol) of triethylamine and a spatula-tip of DMAP. After 0.04 ml (0.04 g, 0.40 mmol) of acetic anhydride had been added, the mixture was stirred at room temperature for 2 h and then the solvent was removed under reduced pressure. The residue was purified by column chromatography with cyclohexane/ethyl acetate (1:1). 0.074 g (0.23 mmol, 63.9%) of 6-(diphenylphosphino)-2-acetylaminopyridine was obtained as a beige-colored solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography with cyclohexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-6a49fea9d7b54094b170bdef47811384
Source dataset
uspto-grants-2006_05
Patent number
US07049473B2

Reaction notes

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