4-(5-Cyclopropyl-1,2-oxazol-3-yl)pyridine → HCID 68139836, compound

HRID 1076681Notes

Reaction equation

HRID 1076681 reaction equation
C1(C2ON=C(C3C=CN=CC=3)C=2)CC1.[CH:15]1([C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[O:20][N:19]=2)[CH2:17][CH2:16]1.[H][H]>[Pt]=O.C(O)C>[NH2:19][C:18]([CH:15]1[CH2:17][CH2:16]1)=[CH:22][C:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)=[O:20]

Participants

6

Reactant 3

HCID 123605774-(5-Cyclopropyl-1,2-oxazol-3-yl)pyridineHCID 12360578HCID 12360578, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68139836HCID 68139836, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A 1.0 g. sample of the mixture of 4-(5-cyclopropyl-3-isoxazolyl)pyridine and 4-(3-cyclopropyl-5-isoxazolyl)pyridine, obtained as described in Examples 2 and 3, is mixed with 0.125 g. of platinum oxide and 75 ml. of ethanol. This mixture is treated with hydrogen on a Parr apparatus at 40 psi for 2 hours at room temperature. The mixture is filtered and the filtrate concentrated to yield a solid. Recrystallization from ethyl acetate-petroleum ether (30°-60°C.) provides 3-amino-3-cyclopropyl-1-(4-pyridyl)-2-propen-1-one as white crystals, melting point 124°-125°C. The ethyl acetate-petroleum ether (30°-60°C.) filtrate is concentrated to a solid which is recrystallized from aqueous ethanol to give 4-(5-cyclopropyl-3-isoxazolyl)pyridine as white crystals, melting point 78°-79.5°C., mmr spectrum δ6.85 (DMSO-d6, s, 4-isoxazolyl H).

Workup

  1. customobtained
  2. additionis mixed with 0.125 g
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated
  5. customto yield a solid
  6. customRecrystallization from ethyl acetate-petroleum ether (30°-60°C.)

Sources & evidence

ORD record
ord-a60baaae749d40ddafc2ea13b55b4363
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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