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

HRID 1435849노트

반응식

HRID 1435849 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

(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)−.

후처리

  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)

출처 및 근거

ORD 기록
ord-bd2c2043dadd4b0bbe53d2c49219a2e9
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618959B2

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