Sodium Chloride → HCID 70392563, compound

HRID 1761464Notes

Reaction equation

HRID 1761464 reaction equation
C[O:2][C:3]([CH:5]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[N:12](C(OCC(Cl)(Cl)Cl)=O)[CH:11]=3)[N:7]([C:29]([O:31][CH2:32][C:33](Cl)([Cl:35])[Cl:34])=[O:30])[CH2:6]1)=O.[NH2:37][NH2:38].[Cl-:39].[Na+]>C(Cl)(Cl)Cl>[Cl:39][C:33]([Cl:34])([Cl:35])[CH2:32][O:31][C:29]([N:7]1[C@H:8]2[C:18]([C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:20]=3[C:10]([CH2:9]2)=[CH:11][NH:12]4)=[CH:19][CH:5]([C:3]([NH:37][NH2:38])=[O:2])[CH2:6]1)=[O:30]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 9321HydrazineHCID 57249165HCID 57249165, compound

Product 1

HCID 70392563HCID 70392563, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

490 mg of the ester (0.8 mmol) in 35 ml of chloroform is stirred together with 12 ml of hydrazine for 25 hours at room temperature. The mixture is then distributed between chloroform and saturated sodium chloride solution, the organic phase is dried with magnesium sulfate and evaporated. The crude product, amounting to 287 mg, is chromatographed on silica gel, thus isolating 193 mg of 9,10-didehydro-6-(2,2,2-trichloroethoxycarbonyl)-8-ergolinecarboxylic acid hydrazide as an oily mixture of isomers (55% of theory).

Workup

  1. dry with materialthe organic phase is dried with magnesium sulfate
  2. customevaporated
  3. customThe crude product, amounting to 287 mg, is chromatographed on silica gel

Sources & evidence

ORD record
ord-db43be9db68948ada64dbc242f9be5ee
Source dataset
uspto-grants-1989_05
Patent number
US04826852

Reaction notes

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