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

HRID 375522노트

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HRID 375522 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매

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온도
5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d458ffb65c6f431db06977d623c64fbf
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486515

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