Ethyl Acetate → 3-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one

HRID 131168

반응식

HRID 131168 반응식
[OH:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20](=[O:23])[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[NH2:14][C:13]1[C:3]2[CH:4]=[C:5]3[C:10]([CH2:9][CH2:8][CH2:7][C:6]3=[O:12])=[CH:11][C:2]=2[O:1][C:21]=1[C:20](=[O:23])[C:19]1[CH:24]=[CH:25][CH:26]=[C:17]([O:16][CH3:15])[CH:18]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 218649643-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

생성물 1

HCID 218649513-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one수율 24%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 3-hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile from method II-6 (45 mg, 0.24 mmol) and 3-methoxyphenacyl bromide (60 mg, 0.26 mmol, 1.1 eq) in anhydrous N,N-dimethylformamide (2 mL) was added potassium carbonate (66 mg, 0.48 mmol, 2 eq). The reaction mixture was shaken at 90° C. for 17 h. The mixture was cooled to room temperature and poured into ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice. Combined the organic layers and evaporated in vacuo. The crude product was washed with methanol and gave 19 mg (24%) of 3-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one as a yellow solid. 1H-NMR (DMSO-d6) δ 8.72 (s, 1H), 7.68 to 7.42 (m, 5H), 7.18 to 7.14 (m, 1H). 6.33 (s, 1H), 3.84 (s, 3H), 3.07 (t, J=6.0 Hz, 2H), 2.65 (t, J=6.6 Hz, 2H), 2.50 (m, 2H); MS LC-MS (MH+=336.2); Rf=0.62, 50% ethyl acetate-hexane.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate twice
  3. customevaporated in vacuo
  4. washThe crude product was washed with methanol

출처 및 근거

ORD 기록
ord-b26eb55805d646b0a03f785cdc8cc451
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384947B2

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