Acetic Acid → HCID 178488951, compound

HRID 1722010Notes

Reaction equation

HRID 1722010 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([N+:15]([O-])=O)=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.[H][H].[CH3:20][C:21](O)=[O:22]>C(OC(=O)C)(=O)C.[Pt]>[C:21]([NH:15][C:11]1[NH:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:13][C:12]=1[CH3:14])(=[O:22])[CH3:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 135671327HCID 135671327, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178488951HCID 178488951, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 41 (3.5 g, 0.015 mole) dissolved in glacial HOAc (35 ml)-acetic anhydride (105 ml) was hydrogenated at 50 psi over 5% platinum on charcoal catalyst (0.75 g) until uptake of hydrogen was complete. Catalyst was filtered off and the filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in H2O (50 ml) and heated on a steam bath for 1 hour. The cooled solution was washed with ether (4×10 ml) and then evaporated to dryness in vacuo. Recrystallization of the residue from CHCl3 gave 3.07 g (84%) of 42 in two crops; m.p. 202°-204° C.

Workup

  1. filtrationCatalyst was filtered off
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in H2O (50 ml)
  4. temperatureheated on a steam bath for 1 hour
  5. washThe cooled solution was washed with ether (4×10 ml)
  6. customevaporated to dryness in vacuo
  7. customRecrystallization of the residue from CHCl3

Sources & evidence

ORD record
ord-e711cab2bab3402f8ea26ba25ec941c2
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

Loading…