Hydrochloric Acid → Hydrochloric Acid

HRID 1253006Notes

Reaction equation

HRID 1253006 reaction equation
[C:1]1([C:15]([OH:16])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=[C:6]([N+:7]([O-:9])=[O:8])[CH:5]=1)[N+:2]([O-:4])=[O:3].[NH2:17][CH2:18][C:19](=O)[CH2:20][CH:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1)[CH2:22][CH3:23].[NH2:35][NH:36][C:37]([NH2:39])=[O:38].[ClH:40]>CCO>[ClH:40].[C:11]1([C:15]([OH:16])=[C:1]([N+:2]([O-:4])=[O:3])[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[CH:10]=1)[N+:12]([O-:14])=[O:13].[NH2:17][CH2:18][C:19](=[N:35][NH:36][C:37]([NH2:39])=[O:38])[CH2:20][CH:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1)[CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5196SemicarbazideHCID 20138234HCID 20138234, compound

Product 2

HCID 313Hydrochloric AcidHCID 86742184HCID 86742184, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the amino ketone picrate ((9) 6.4 g, 0.133 mol), semicarbazide.HCl (2.6 g, 0.023 mol) and 190 ml of 70% EtOH was stirred at room temperature for 90 hours. The solid was collected and washed with 70% EtOH, and the filtrate was evaporated and similarly retreated with 1.27 g of semicarbazide.HCl in 75 ml of 70% EtOH to afford 0.76 g of yellow crystals (10), mp 200°-201° C. The original solid above was treated with 225 ml of warm EtOH and the insoluble portion collected to give 2.67 g, ml 196°-197° C. The combined mother liquors were evaporated and retreated with 0.84 g of semicarbazide.HCl in 61 ml of 70% EtOH to afford another 1.66 g of (10), mp 200°-201° C., for a total yield of (10) of 5.09 (71%).

Workup

  1. customThe solid was collected
  2. washwashed with 70% EtOH
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-60b4414f8a5e4a65bb68cbe9ef39d7a5
Source dataset
uspto-grants-1988_05
Patent number
US04746659

Reaction notes

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