Acetic Acid → HCID 86741486, compound

HRID 978452Notes

Reaction equation

HRID 978452 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([N+:27]([O-])=O)[CH:23]=4)[NH:18][C:17]3=[O:30])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.S1C=CC=C1.[C:38]([OH:41])(=[O:40])[CH3:39].[H][H].C[OH:45]>[Pt]>[C:25]([OH:26])(=[O:45])/[CH:24]=[CH:39]\[C:38]([OH:41])=[O:40].[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([NH:27][C:38](=[O:40])[CH3:39])[CH:23]=4)[NH:18][C:17]3=[O:30])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 8030ThiopheneHCID 13851177HCID 13851177, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86741486HCID 86741486, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

A mixture of 1.2 parts of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-6-nitro-2,4(1H,3H)-quinazolinedione, 0.5 parts of a solution of thiophene in methanol 4% and 100 parts of acetic acid was hydrogenated at normal pressure and at room temperature with 1 part of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and 10 parts of acetic acid anhydride were added to the filtrate. The whole was stirred and refluxed for 3 hours. After evaporation, water was added to the residue and the whole was treated with ammonia. The precipitated product was filtered off and converted into the (Z)-2-butenedioate salt in ethanol. From the latter the salt was crystallized at -5° C. The product was filtered off and dried, yielding 0.4 parts (32%) of N-[3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-1,2,3,4-tetrahydro-2,4-dioxo-6-quinazolinyl]-acetamide (Z)-2-butenedioate(1:1).monohydrate; mp. 170.7° C. (15).

Workup

  1. filtrationthe catalyst was filtered off
  2. addition10 parts of acetic acid anhydride were added to the filtrate
  3. temperaturerefluxed for 3 hours
  4. customAfter evaporation, water
  5. additionwas added to the residue
  6. additionthe whole was treated with ammonia
  7. filtrationThe precipitated product was filtered off
  8. customFrom the latter the salt was crystallized at -5° C
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-01f530f9e45744049f1a70fe2990c51b
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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