Sodium Bicarbonate → 2H-1,2-Benzoxazin-3(4H)-one

HRID 375522

反応式

HRID 375522 の反応式
[O:1]=[C:2]1[NH:7]C2C=C([N+]([O-])=O)C=CC=2O[CH2:3]1.N[C:16]1[CH:21]=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][C:17]=1[OH:25].C(=O)(O)[O-].[Na+]>C(C(C)=O)C(C)C>[O:25]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:3][C:2](=[O:1])[NH:7]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-oneHCID 36133892-Amino-4-Nitrophenol

生成物 1

HCID 199374482H-1,2-Benzoxazin-3(4H)-one

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

反応条件

温度
5 °C

実験手順

3-Oxo-6-nitro-3,4-dihydro-2H-1,4-benzoxazine. A solution of 2-amino-4-nitrophenol (8.80 g), in methyl isobutyl ketone (30 mL) was treated with sodium bicarbonate (11.5 g) and distilled water (35 mL). The mixture was cooled to 5° C. under a nitrogen atmosphere, treated dropwise with chloroacetyl chloride (5.0 mL) and then heated to reflux for 18 hours. A brown solid was collected from the cooled mixture by filtration. The solid was dried under vacuum at 50° C. for 24 hours yielding benzoxazinone (10.5 g) as a brown solid; mp 235°-236° C.; MS: m/z=195(M+1); NMR: 4.76 (s,2), 7.14 (d,1), 7.74 (d,1), 7.82 (dd,1), 11.07 (broad s,1).

後処理

  1. distillationdistilled water (35 mL)
  2. additiontreated dropwise with chloroacetyl chloride (5.0 mL)
  3. temperatureheated
  4. temperatureto reflux for 18 hours
  5. filtrationA brown solid was collected from the cooled mixture by filtration
  6. customThe solid was dried under vacuum at 50° C. for 24 hours

出典と根拠

ORDレコード
ord-d458ffb65c6f431db06977d623c64fbf
出典データセット
uspto-grants-1996_01
特許番号
US05486515

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