2,6-Lutidine → (+/-)-3-Methoxy-5,6,9,10,11,12,13,13a-octahydroisoquino[2,1-g][1,6]naphthyridin-8-one

HRID 484392

反応式

HRID 484392 の反応式
O=[C:2]1[CH2:11][CH:10]2[N:5]([CH2:6][CH2:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=32)[C:4](=[O:18])[CH2:3]1.Br.Br[CH2:21][CH2:22][CH2:23][NH2:24].N1C(C)=CC=CC=1C>C(O)CCC>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:9]2[CH:10]3[N:5]([C:4](=[O:18])[C:3]4[CH2:21][CH2:22][CH2:23][NH:24][C:2]=4[CH2:11]3)[CH2:6][CH2:7][C:8]=2[CH:15]=1

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 787013-Bromopropylamine hydrobromideHCID 10421964HCID 10421964、化合物

生成物 1

HCID 9971129(+/-)-3-Methoxy-5,6,9,10,11,12,13,13a-octahydroisoquino[2,1-g][1,6]naphthyridin-8-one収率 70.3%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
10 °C

実験手順

A solution of 27.3 Kg of 2,4-dioxo-9-methoxy-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine, 19.6 Kg of 3-bromopropylamine hydrobromide and 22.8 Kg of 2,6-lutidine in 70 litres of n-butanol was refluxed for 1 hour. Butanol and excess 2,6-lutidine were removed under reduced pressure, and the solid residue dissolved in 150 litres of methanol at reflux temperature. The temperature was maintained above 70° C. while 150 litres of water was added. The mixture was cooled to 10° C., the precipitate filtered off and washed with 1:1 aqueous methanol. This product was recrystallized from a mixture of 150 Kg of methanol and 175 Kg of water. Drying under vacuum at 80° C. for three days gave 17.9 Kg of (±)-3-methoxy-5,6,9,10,11,12,13,13a-octahydroisoquino[2,1-g][1,6]naphthyridin-8-one, m.p. 202°-205° C.

後処理

  1. customButanol and excess 2,6-lutidine were removed under reduced pressure
  2. dissolutionthe solid residue dissolved in 150 litres of methanol
  3. temperatureat reflux temperature
  4. temperatureThe temperature was maintained above 70° C. while 150 litres of water
  5. additionwas added
  6. filtrationthe precipitate filtered off
  7. washwashed with 1:1 aqueous methanol
  8. customThis product was recrystallized from a mixture of 150 Kg of methanol and 175 Kg of water
  9. customDrying under vacuum at 80° C. for three days

出典と根拠

ORDレコード
ord-5a614bc5fa1147939e6b3873cfc69aa2
出典データセット
uspto-grants-1993_07
特許番号
US05231181

関連ノート

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