Acetic Anhydride → HCID 118307491, compound

HRID 2283226Notes

Reaction equation

HRID 2283226 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8][NH2:9])[CH:7]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C(OCC)(=O)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=1)[CH2:8][NH:9][C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 53401485HCID 53401485, compound

Product 1

HCID 118307491HCID 118307491, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 13 (2.5 g, 10.82 mmol) in pyridine (20 mL) was added acetic anhydride (2 mL, 21.60 mmol) and the mixture was stirred at room temperature for 12 h. The reaction was added ethyl acetate (30 mL) and the organic layer was washed sequentially with H2O (20 mL), IN HCl (15 mL×3), brine (15 mL) and dried over Na2SO4 and evaporated to get the title compound as an off-white solid (2.89 g, 98%). IR (KBr) vmax. cm−1: 3419 (NH), 3062 (Ar—H), 2925 (Alph-H), 1695 (C═O), 1604, 1564 (C═C), 1520, 1435 (NO2), 1232 (C—N), 1168 (C—O). 1H NMR (500 MHz, CDCl3) δ=2.19 (s, 3H, CH3); 5.50 (s, 2H, CH2); 7.63 (dd, 1H, J=2.3, 8.6 Hz, H-4); 7.75 (d, 1H, J=2.3, H-6), 8.00 (d, 1H, J=8.6 Hz, H-3). 13C NMR (125.7 MHz, CDCl3) δ=20.78 (CH3), 62.27 (CH2), 126.58 (C-3), 129.03 (C−1), 131.73 (C-6), 131.82 (C-4), 134.34 (C-5), 145.33 (C-2), 170.10 (CO). Calculated (%) for C9H9BrN2O3 (271.98); C, 39.58; H, 3.32; N, 10.26. found (%); C, 39.52; H, 3.36; N, 10.20.

Workup

  1. washthe organic layer was washed sequentially with H2O (20 mL), IN HCl (15 mL×3)
  2. dry with materialbrine (15 mL) and dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-b0f57f5a4cc94cb5ac9614584cc51bee
Source dataset
uspto-grants-2015_09
Patent number
US09145388B2

Reaction notes

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