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

HRID 55350

Reaction equation

HRID 55350 reaction equation
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]

Participants

8

Reactant 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, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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-6carboxylic hydrazide. m.p. 199°-201° C.

Workup

  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

Sources & evidence

ORD record
ord-930ce4cbead84118a7f337f936ae3108
Source dataset
uspto-grants-1997_04
Patent number
US05624944

Linked notes

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