ethyl 2-(4-formyl-2-nitrophenoxy)acetate → 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

HRID 1435849Notes

Reaction equation

HRID 1435849 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[N+:15]([O-])=O)C>C(O)(=O)C.[Fe]>[O:3]=[C:4]1[NH:15][C:8]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5]1

Participants

4

Reactant 1

HCID 5305379ethyl 2-(4-formyl-2-nitrophenoxy)acetate

Product 1

HCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeYield 66.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

(4-Formyl-2-nitrophenoxy)acetic acid ethyl ester (1.9 g) in acetic acid (40 mL) was treated with iron powder (4.2 g) and the mixture was stirred at 60° C. for 0.75 hours, filtered and evaporated to dryness. It was partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic fraction was chromatographed on silica gel (ethyl acetate) to give a white solid (0.88 g). MS (−ve ion electrospray) m/e 176 (M−H)−.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customIt was partitioned between aqueous sodium bicarbonate and ethyl acetate
  4. customThe organic fraction was chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-bd2c2043dadd4b0bbe53d2c49219a2e9
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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