Acetic Anhydride → 8-ACETYLAMINOQUINOLINE

HRID 720729Notes

Reaction equation

HRID 720729 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20].C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][C:19](=[O:21])[CH3:20])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 113598-AminoquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 365918-ACETYLAMINOQUINOLINEYield 101.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8-aminoquinoline (33.37 g, 0.231 mol), DMAP (4-dimethylaminopyridine) (1.40 g, 0.011 mol) and triethylamine (Et3N) (37 mL, 0.265 mol) in CH2Cl2 (methylene chloride) (275 mL) was added acetic anhydride (Ac2O) (26.5 mL, 0.281 mol). After 20 hours the reaction mixture was poured into a saturated aqueous solution of NaHCO3 (sodium bicarbonate). The phases were separated and the aqueous phase was extracted with ether (3×150 mL). The combined organic phases were dried (Na2SO4) (sodium sulfate), filtered and concentrated in vacuo to provide 43.56 g (100%) of N-(quinolin-8-yl)-acetamide as a beige solid. This material was used without further purification in subsequent steps. 1H NMR (CDCl3) δ 2.35 (s, 3H), 7.42–7.56 (m, 3H), 8.15 (dd, 1H, J=1.5, 8.4 Hz), 8.76 (dd, 1H, J=1.8, 7.2 Hz), 8.79 (dd, 1H, J=1.5, 4.2 Hz), 9.78 (br s, 1H); 13C NMR (CDCl3) δ 25.5, 116.8, 121.8, 122.0, 127.8, 128.3, 134.9, 136.8, 138.6, 148.5, 169.2. ES-MS m/z 187 (M+H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ether (3×150 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4) (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa93df09e4ba47f9b4c5c6279afafd05
Source dataset
uspto-grants-2006_11
Patent number
US07135570B2

Reaction notes

Loading…