Tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate → 2-(6-Methoxy-5-methyl-3-nitropyridin-2-yl)acetic acid

HRID 386500Notes

Reaction equation

HRID 386500 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])[C:6]([N+:17]([O-:19])=[O:18])=[CH:5][C:4]=1[CH3:20]>C(O)(C(F)(F)F)=O.CCCCCC>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([OH:12])=[O:11])[C:6]([N+:17]([O-:19])=[O:18])=[CH:5][C:4]=1[CH3:20]

Participants

4

Reactant 1

HCID 44596705Tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate

Product 1

HCID 445967062-(6-Methoxy-5-methyl-3-nitropyridin-2-yl)acetic acidYield 94.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8058HexaneSolvent

Procedure

A solution of tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate (83.0 g, 294 mmol) in TFA (200 mL) was heated in a hot water bath for 1 h. The solution was concentrated in vacuo to give a brown oil. The oil was diluted with hexane and stirred. The resulting solid was collected by filtration and air dried to give 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetic acid (62.8 g, 94% yield) as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.70 (s br, 1H), 8.20 (s, 1H), 4.25 (s, 2H), 4.03 (s, 3H), 2.24 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 175.59, 163.80, 146.52, 139.16, 135.30, 121.53, 54.86, 42.88, 15.32. An analytical sample was recrystallized from hexane: mp 135-137° C. Anal. calcd. for C9H10N2O5: C, 47.79; H, 4.46; N, 12.39. Found: C, 47.65; H, 4.14; N, 12.30.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give a brown oil
  3. filtrationThe resulting solid was collected by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-b4015171c287414aafdc2537f10e3a9d
Source dataset
uspto-grants-2013_02
Patent number
US08372847B2

Reaction notes

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