Acetic Acid → 7-Methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 989340

反応式

HRID 989340 の反応式
C([Li])CCC.[C:6](#[N:8])[CH3:7].CN(/[CH:12]=[N:13]/[C:14]1[C:15]([C:26]([O:28]C)=O)=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[C:19]([O:24][CH3:25])[CH:18]=2)C.C(O)(=O)C>O1CCCC1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][C:22]2[CH:23]=[C:14]3[C:15]([C:26](=[O:28])[C:7]([C:6]#[N:8])=[CH:12][NH:13]3)=[CH:16][C:17]=2[CH:18]=1

参加物

6

反応物 4

HCID 176Acetic Acid2 回HCID 6342AcetonitrileHCID 178418339ButyllithiumHCID 178496951HCID 178496951、化合物

生成物 1

HCID 98136637-Methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of 4.75 mL (11.88 mmol) of n-butyllithium (2.5M in hexane) in 4.0 mL of tetrahydrofuran at −78° C. is added dropwise a solution of 0.68 mL (13.1 mmol) of acetonitrile in 6.8 mL of tetrahydrofuran. After completion of addition, the suspension is stirred for 10 minutes. To this is added 1.36 g (4.75 mmol) of methyl 3-{[(E)-(dimethylamino)methylidene]amino}-7-methoxy-2-naphthoate in 32 mL of tetrahydrofuran dropwise. The resulting reaction mixture is stirred at −78° C. for 1 hour, at −5° C. for 1 hour and at room temperature for 15 minutes. The reaction mixture is again cooled to −78° C. and 1.72 g (28.6 mmol) of acetic acid is added dropwise. After addition of the acetic acid, the reaction mixture is allowed to warm to room temperature. The precipitate is collected by filtration and washed sequentially with water, acetonitrile and methanol. After drying in vacuo, this yields 796.9 mg (67%) of 7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile as a deep yellow solid, mp>260° C.

後処理

  1. additionAfter completion of addition
  2. customThe resulting reaction mixture
  3. stirringis stirred at −78° C. for 1 hour, at −5° C. for 1 hour and at room temperature for 15 minutes
  4. temperatureto warm to room temperature
  5. filtrationThe precipitate is collected by filtration
  6. washwashed sequentially with water, acetonitrile and methanol
  7. customAfter drying in vacuo

出典と根拠

ORDレコード
ord-e64447100648458bb0aacd9594b0b3c2
出典データセット
uspto-grants-2003_10
特許番号
US06638929B2

関連ノート

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