Acetic Anhydride → HCID 11437271, compound

HRID 431742Notes

Reaction equation

HRID 431742 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](CCO)=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=1>N1C=CC=CC=1.CCOC(C)=O>[C:5]([O:4][CH2:1][CH2:2][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([NH2:8])=[CH:10][C:11]=1[N+:22]([O-:24])=[O:23])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 18761442HCID 18761442, compound

Product 1

HCID 11437271HCID 11437271, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (4.0 mL, 42.39 mmol) was added to a solution of 2-[4-amino-2-nitronaphthalen-1-yl]ethanol (3.3 g, 14.21 mmol) in dry pyridine (33 mL) at room temperature and stirred for 2 hr. The mixture was diluted with AcOEt (100 mL). The organic layer was washed with H2O (30 mL), saturated aqueous NaHCO3 (30 mL), saturated aqueous NaCl (30 mL), and then the organic layer was dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography (33% AcOEt-Petroleum ether) afforded 2-[4-amino-2-nitronaphthalen-1-yl]ethyl acetate (1.0 g, 26%) as an orange solid.; mp 108-110 ° C.; 1H NMR (CDCl3, 500 MHz) δ 8.33 (d, 8.5, 1H), 7.84 (dd, 8.0, 0.5, 1H), 7.70 (dt, 7.5, 0.5, 1H), 7.64 (dt, 8.5, 1.5, 1H), 7.11 (s, 1H), 4.44 (t, 8.0, 2H), 4.38 (brs, 2H), 3.49 (t, 8.0, 2H), 2.06 (d, 0.5, 3H); FABMS (NBA) m/z 274 (M+), IR (neat) 3381, 1728, 1636, 1589, 1516, 1469, 1437, 1342, 1241, 1041, 754 cm−1.

Workup

  1. washThe organic layer was washed with H2O (30 mL), saturated aqueous NaHCO3 (30 mL), saturated aqueous NaCl (30 mL)
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df4366a6ec254fd6af8eafa6ac21e55b
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

Loading…