Hydrochloric Acid → Ethyl (2,4-dinitronaphthalen-1-yl)acetate

HRID 431730Notes

Reaction equation

HRID 431730 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:18](C(OCC)=O)[C:19]([O:21][C:22](C)(C)[CH3:23])=[O:20])([O-:4])=[O:3]>CCOC(C)=O>[N+:2]([C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11452450t-Butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate

Product 1

HCID 11358597Ethyl (2,4-dinitronaphthalen-1-yl)acetateYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Concentrated HCl (1.5 mL) was added to a solution of t-butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate (0.60 g, 1.48 mmol) in AcOEt (6 mL), and the mixture was stirred overnight. The mixture was diluted with AcOEt (30 mL), washed with H2O (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Recrystallization (Ether) afforded ethyl (2,4-dinitronaphthalen-1-yl)acetate (0.31 g, 69%) as a pale orange solid. M.p. 132-134° C.; 1H NMR (CDCl3, 500 MHz) δ 8.71 (s, 1H), 8.61 (d, 8.5, 1H), 8.30 (d, 8.5, 1H), 7.92 (dt, 1.0, 8.5, 1H), 7.86 (dt, 1.5, 8.5, 1H), 4.51 (s, 2H), 4.22 (q, 7.5, 2H), 1.27 (t, 7.5, 3H); 304 (M−); IR (neat) 3087, 2989, 1732, 1528, 1422, 1355, 1204, 1169, 1027, 889, 832, 779 cm−1. FABMS (NBA) m/z 305 (M+H+).

Workup

  1. washwashed with H2O (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customRecrystallization (Ether)

Sources & evidence

ORD record
ord-b0fb057b20384efe815c6d151b194bf9
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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