Diethyl Malonate → HCID 54403188, compound

HRID 1076235Notes

Reaction equation

HRID 1076235 reaction equation
ClC1C=CC(C=C([N+]([O-])=O)C2C=CC=CC=2)=CC=1.[Na].C(OCC)(=O)CC(OCC)=O.[C:31]([CH:36]([CH:42]([C:53]1[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=1)[CH:43]([N+:50]([O-])=O)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:37](OCC)=[O:38])([O:33]CC)=[O:32]>>[C:31]([CH:36]1[CH:42]([C:53]2[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=2)[CH:43]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[NH:50][C:37]1=[O:38])([OH:33])=[O:32]

Participants

5

Reactant 4

HCID 7761Diethyl MalonateHCID 4111184HCID 4111184, compoundHCID 5360545SodiumHCID 54029746HCID 54029746, compound

Product 1

HCID 54403188HCID 54403188, compound

Procedure

The 3-carboxy-4-p-chlorophenyl-5-phenyl-2-pyrrolidinone (after recrystallization from ethanol M.P. : 184°C. (decomposition)) was prepared by condensing 1-p-chlorophenyl-2-nitro-2-phenyl-ethylene with the sodium derivative of diethyl malonate, reduction of the obtained ethyl 2-carbethoxy-3-p-chlorophenyl-4-nitro-4-phenyl-butanoate (M.P. : 148°-149°C. (recrystallized from ethanol) by means of hydrogen under pressure in presence of Raney cobalt and hydrolysis of the resulting 3-carbethoxy-4-p-chlorophenyl-5-phenyl-2-pyrrolidinone (M.P. : 198°C. (recrystallized from toluene)).

Workup

  1. custom148°-149°C. (recrystallized from ethanol) by means of hydrogen under pressure
  2. customin presence of Raney cobalt and hydrolysis of the resulting 3-carbethoxy-4-p-chlorophenyl-5-phenyl-2-pyrrolidinone (M.P. : 198°C. (recrystallized from toluene))

Sources & evidence

ORD record
ord-8f3095c405224ffe936085362b811ad2
Source dataset
uspto-grants-1976_05
Patent number
US03956314

Reaction notes

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