Methyl chloroformate → 6-bromo-7,8,9,9a-tetrahydro-3H-naptho[1,8-de][1,3]oxazine-2-one

HRID 2114545노트

반응식

HRID 2114545 반응식
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Br:18])=[C:11]2[C:16]=1C(O)[CH2:14][CH2:13][CH2:12]2.C(=O)([O-])[O-].[K+].[K+]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Br:18][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:2](=[O:3])[O:4][CH:5]3[CH2:14][CH2:13][CH2:12][C:11]=1[C:16]=23

참가 물질

6

반응물 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 692133418-Amino-5-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

생성물 1

HCID 692149946-bromo-7,8,9,9a-tetrahydro-3H-naptho[1,8-de][1,3]oxazine-2-one

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

To prepare this compound, DMAP (6 mg, 0.043 mmol) and methyl chloroformate (27 mg, 0.29 mmol) were added to a solution of 8-amino-5-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (70 mg, 0.29 mol) in 1.5 mL pyridine at −10° C. The reaction was stirred for 0.5 hour, then extracted with ethyl acetate and water. The organic layer was washed sequentially with 2% aqueous HCl solution, water, and brine an then was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in 1.5 ml dry DMF and then potassium carbonate (80 mg, 0.58 mmol) was added. That suspension was heated at 100° C. for 2 hours, and was extracted with EtOAc and water. The organic layer from that extraction was washed sequentially with 2% aqueous HCl, water, and brine and was then dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 6-bromo-7,8,9,9a-tetrahydro-3H-naptho[1,8-de][1,3]oxazine-2-one. 1H NMR (500 MHz, CDCl3) δ 8.55 (broad s, 1H), 7.41 (d, J=8.2, 1H), 6.60 (d, J=8.4, 1H), 5.3-5.4 (m, 1H), 2.90 (dd, J=17.8, 5.0, 1H), 2.55-2.65 (m, 1H), 2.40-2.50 (m, 1H), 2.15-2.25 (m, 1H), 1.70-1.90 (m, 2H).

후처리

  1. extractionextracted with ethyl acetate and water
  2. washThe organic layer was washed sequentially with 2% aqueous HCl solution, water, and brine
  3. dry with materialan then was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 1.5 ml dry DMF
  7. extractionwas extracted with EtOAc and water
  8. extractionThe organic layer from that extraction
  9. washwas washed sequentially with 2% aqueous HCl, water, and brine
  10. dry with materialwas then dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bd986f9336e54e56bef3f4daec3210dd
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435733B2

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