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

HRID 1435849ノート

反応式

HRID 1435849 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

(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)−.

後処理

  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)

出典と根拠

ORDレコード
ord-bd2c2043dadd4b0bbe53d2c49219a2e9
出典データセット
uspto-grants-2009_11
特許番号
US07618959B2

反応ノート

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