Methyl morpholine oxide → Methyl 3-formyl-2-nitrobenzoate

HRID 2090523Notes

Reaction equation

HRID 2090523 reaction equation
Br[CH2:2][C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C[N+]1([O-])CC[O:20]CC1>CC#N.CCOC(C)=O>[CH:2]([C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:20]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22509333Methyl 3-(bromomethyl)-2-nitrobenzoate

Product 1

HCID 44549250Methyl 3-formyl-2-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (A2) (1.0 eq.) and 4 Å mol. sieves in MeCN (0.2M) at RT was added NMMO (2.0 eq.) and the reaction mixture was stirred for 1.5 hr under N2 atmosphere. Then, the mixture was diluted with EtOAc, filtered and the filtrate was washed with H2O, 1N HCl, brine and dried (Na2SO4). Evaporation of the solvent gave (A3) as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ 9.96 (1H, s), 8.26 (1H, d, J=7.9 Hz), 8.18 (1H, d, J=7.9 Hz), 7.77 (1H, t, J=7.9 Hz), 3.93 (3H, s). MS (ES) C9H7NO5 requires: 209. found: 208 (M−H)−.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with H2O, 1N HCl, brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3535cbaaecad43648411f387e8ac55b5
Source dataset
uspto-grants-2013_05
Patent number
US08436185B2

Reaction notes

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