Acetic Acid → 7,8-Dimethoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 989288노트

반응식

HRID 989288 반응식
C([Li])CCC.[C:6](#[N:8])[CH3:7].CO[C:11]([C:13]1[C:22]([N:23]=[CH:24]N(C)C)=[CH:21][C:20]2[C:15](=[CH:16][C:17]([O:30][CH3:31])=[C:18]([O:28][CH3:29])[CH:19]=2)[CH:14]=1)=[O:12].C(O)(=O)C>C1COCC1.O>[CH3:31][O:30][C:17]1[C:18]([O:28][CH3:29])=[CH:19][C:20]2[CH:21]=[C:22]3[C:13]([C:11](=[O:12])[C:7]([C:6]#[N:8])=[CH:24][NH:23]3)=[CH:14][C:15]=2[CH:16]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 98799543-(Dimethylaminomethyleneamino)-6,7-dimethoxy-naphthalene-2-carboxylic acid methyl esterHCID 178418339Butyllithium

생성물 1

HCID 99435817,8-Dimethoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of 2.6 mL (6.3 mmol) of n-butyllithium (2.5M in hexane) in 2.0 ml of THF is added dropwise a solution of 0.36 mL (6.9 mmol) of acetonitrile in 6 mL of THF at −78° C. After completion of addition, the suspension is stirred for 15 minutes. To this is added 496.7 mg (1.57 mmol) of 3-(dimethylaminomethyleneamino)-6,7-dimethoxy-naphthalene-2-carboxylic acid methyl ester in 15 mL of THF dropwise. The resulting reaction mixture is stirred at −78° C. for 1.5 hours. Then 942.8 mg (15.7 mmol) of acetic acid is added dropwise. The reaction mixture is warmed to room temperature and is diluted with water. The precipitate is collected by filtration and washed with water and methanol. After drying in vacuo, this yields 406.0 mg(92.3%) of the product as a light brown solid, mp>265° C.

후처리

  1. additionAfter completion of addition
  2. customThe resulting reaction mixture
  3. stirringis stirred at −78° C. for 1.5 hours
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water and methanol
  6. customAfter drying in vacuo

출처 및 근거

ORD 기록
ord-75ef102a975047d1a60e3574acfe484e
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638929B2

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