HCID 88622800, compound → N-[2-cyano-3-(1,4-dihydro 1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-propanoyl]-glycine

HRID 21544Notes

Reaction equation

HRID 21544 reaction equation
[C:1]([CH:3]([C:12]([C:14]1[C:15]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:16]=2[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:18]=1)=[O:13])[C:4]([NH:6][CH2:7][C:8]([O:10]C)=[O:9])=[O:5])#[N:2]>[OH-].[K+].C(O)C>[C:1]([CH:3]([C:12]([C:14]1[C:15]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:16]=2[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:18]=1)=[O:13])[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])#[N:2]

Participants

4

Reactant 1

HCID 88622800HCID 88622800, compound

Product 1

HCID 19932559N-[2-cyano-3-(1,4-dihydro 1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-propanoyl]-glycineYield 73.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 14797Potassium HydroxideSolvent

Procedure

N-[2-Cyano-3-(1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl) -3-oxo-propanoyl]-glycine, methyl ester (1.7 g), is suspended in 1% KOH solution in 95% ethanol (60 ml) and heated under stirring at the reflux temperature for 30 minutes. After cooling the precipitate is filtered and washed with ethanol, then dissolved in water. The aqueous basic solution is extracted with ethyl acetate and then acidified to pH 3 with 2N HCl. The precipitate is extracted with ethyl acetate and the organic solution washed with N HCl and then with water until neutral. Evaporation to dryness in vacuo gives a residue which is crumbled with ethanol to yield 1.2 g of N-[2-cyano-3-(1,4-dihydro 1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-propanoyl]-glycine, m.p. 247°-249° C. dec.

Workup

  1. temperatureheated
  2. temperatureAfter cooling the precipitate
  3. filtrationis filtered
  4. washwashed with ethanol
  5. dissolutiondissolved in water
  6. extractionThe aqueous basic solution is extracted with ethyl acetate
  7. extractionThe precipitate is extracted with ethyl acetate
  8. washthe organic solution washed with N HCl
  9. customEvaporation to dryness in vacuo
  10. customgives a residue which

Sources & evidence

ORD record
ord-42b2a26123bd4546b201c7b99db3fab2
Source dataset
uspto-grants-1995_06
Patent number
US05424308

Reaction notes

Loading…