Methanol → HCID 57722728, 화합물

HRID 1986894노트

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HRID 1986894 반응식
[H-].[Na+].CO.[C:5](/[C:8](=[C:13](\[C:15]1[C:24]([NH:25][C:26]([O:28]CC)=O)=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[CH:16]=1)/[OH:14])/C(OC)=O)(=[O:7])[CH3:6]>C1C=CC=CC=1>[C:5]([C:8]1[C:26](=[O:28])[NH:25][C:24]2[C:15]([C:13]=1[OH:14])=[CH:16][C:17]1[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=1[CH:23]=2)(=[O:7])[CH3:6]

참가 물질

5

반응물 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 57722730HCID 57722730, 화합물

생성물 1

HCID 57722728HCID 57722728, 화합물

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
72 °C

실험 절차

To a mixture of sodium hydride (95%) (0.70 g, 29 mmol, 2.6 equiv) in benzene (100 mL) at 23° C. under nitrogen was added methanol (2.5 mL, 2.0 g, 62 mmol, 5.4 equiv) dropwise over 10 min. After stirring for an additional 5 min, methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}-3-hydroxyprop-2-enoate (1-4) (4.1 g, 11 mmol, 1 equiv) was added and the resulting mixture was heated at 72° C. for 20 h. The solvent was evaporated under reduced pressure and the solid residue was suspended in water (50 mL) for 30 min followed by 1 N aqueous hydrochloric acid solution (100 mL) for an additional 30 min with stirring. The solid was filtered, washed with water (100 mL) and hexanes (100 mL), and dried to yield 3-acetyl-4-hydroxy-6,7,8,9-tetrahydrobenzo[g]quinolin-2(1H)-one (1-5) as an off-white solid. LRMS m/z (M+H) 258.4 found, 258.1 required.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. waitthe solid residue was suspended in water (50 mL) for 30 min
  3. waitfollowed by 1 N aqueous hydrochloric acid solution (100 mL) for an additional 30 min
  4. stirringwith stirring
  5. filtrationThe solid was filtered
  6. washwashed with water (100 mL) and hexanes (100 mL)
  7. customdried

출처 및 근거

ORD 기록
ord-fd77911f33d547f18b31d9e4f9e756ff
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550477B2

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