Triethylamine → 5-(n-Decoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline

HRID 1583811ノート

反応式

HRID 1583811 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([O:23][CH3:24])[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH:26]([CH3:41])[CH2:27][CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:13]([O:12][C:5]1[C:4]([O:23][CH3:24])=[CH:3][C:2]([NH:1][CH:26]([CH3:41])[CH2:27][CH2:28][CH2:29][N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 240534N-(4-Bromopentyl)phthalimide2 回HCID 135359528-Amino-5-decoxy-6-methoxyquinoline

生成物 1

HCID 539727355-(n-Decoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline収率 49.8%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A stirred mixture of 3.65 g of 8-amino-5-decoxy-6-methoxyquinoline and 3.5 g of 4-bromo-1-phthalimidopentane was maintained at 140°-145° while 1 g of triethylamine was added in portions during 1.5 hr. Five more increments of 4-bromo-1-phthalimidopentane (3 g) and triethylamine (1 g) were added at 1.5 hr intervals in the usual manner. The mixture was allowed to cool and extracted with diethyl ether (ca. 300 ml). Treatment of the extract with diethyl ether-hydrochloric acid gave a red oil. The oil was dissolved in chloroform (200 ml) washed with dilute sodium hydroxide (2×30 ml) and water, dried (potassium carbonate) passed through a silica column and concentrated to give 3 g of phthalimide derivative as a red oil. This material was used without further purification.

後処理

  1. additionwas added in portions during 1.5 hr
  2. temperatureto cool
  3. extractionextracted with diethyl ether (ca. 300 ml)
  4. extractionTreatment of the extract with diethyl ether-hydrochloric acid
  5. customgave a red oil
  6. washwashed with dilute sodium hydroxide (2×30 ml) and water
  7. dry with materialdried (potassium carbonate)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a79ff084e0784be6a2b91e31289dc598
出典データセット
uspto-grants-1985_11
特許番号
US04554279

反応ノート

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