Methanol → HCID 57722728、化合物

HRID 1986894ノート

反応式

HRID 1986894 の反応式
[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]

参加物

5

反応物 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 57722730HCID 57722730、化合物

生成物 1

HCID 57722728HCID 57722728、化合物

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
72 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fd77911f33d547f18b31d9e4f9e756ff
出典データセット
uspto-grants-2009_06
特許番号
US07550477B2

反応ノート

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