Potassium Carbonate → (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6carboxylic hydrazide

HRID 263526ノート

反応式

HRID 263526 の反応式
I[C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]=[C:5]3[CH2:11][C@H:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:13][C:3]=1[C:4]=23.[OH:21][C:22]1C=CC=C[N:23]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:35]N>C(#N)C.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([N:14]([CH2:18][CH2:19][CH3:20])[C@H:12]1[CH2:11][C:5]2=[CH:6][NH:7][C:8]3=[CH:9][CH:10]=[C:2]([C:22]([NH:23][NH2:35])=[O:21])[C:3](=[C:4]23)[CH2:13]1)[CH2:16][CH3:17]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 10691283(4S)-6-iodo-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indoleHCID 178516071HCID 178516071、化合物

生成物 1

HCID 70284014(4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6carboxylic hydrazide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5.0 g (13.1 mmol) of (4S)-6-iodo-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole in 250 ml of acetonitrile was added 3.5 g (37 mmol) of 2-hydroxypyridine, 16.9 g (122 mmol) of powdered potassium carbonate, and 0.30 g (0.26 mmol) of tetrakis(triphenylphosphine)palladium. The resultant mixture was heated at 65° C. under a carbon monoxide atmosphere for 14 hours. The cooled mixture was then treated with 2 ml of hydrazine hydrate and stirred for another 15 hours. After filtering, the mixture was concentrated in vacuo to provide a residue. This residue was taken up in methylene chloride and extracted with aqueous tartaric acid solution. The aqueous layer was basified with 1M sodium hydroxide solution and the product was extracted into methylene chloride. Evaporation of solvent in vacuo left an oily solid which, after thorough washing with a 1:2 mixture of toluene and hexane, afforded 0.60 g of (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide. m.p. 199°-201° C.

後処理

  1. filtrationAfter filtering
  2. concentrationthe mixture was concentrated in vacuo
  3. customto provide a residue
  4. extractionextracted with aqueous tartaric acid solution
  5. extractionthe product was extracted into methylene chloride
  6. customEvaporation of solvent in vacuo
  7. waitleft an oily solid which
  8. washafter thorough washing with a 1:2 mixture of toluene and hexane

出典と根拠

ORDレコード
ord-111bd1e6ffcd4f74bc77b06e4cd6bfb9
出典データセット
uspto-grants-1997_07
特許番号
US05643930

反応ノート

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