Methanol → 3-(4-Pyridyl)-4-methyl-5-methoxy-pyrazole

HRID 370442Notes

Reaction equation

HRID 370442 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[N:9][C:10](=[O:13])[C:11]=2[CH3:12])=[CH:3][CH:2]=1.[C:14]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.N(C(OCC)=O)=NC([O-])=O>O1CCCC1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[NH:9][N:8]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 202760543-(4-Pyridyl)-4-methyl-5-pyrazoloneHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 1784942973-(4-Pyridyl)-4-methyl-5-methoxy-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2 °C

Procedure

1.5 mg of 3-(4-pyridyl)-4-methyl-5-pyrazolone, 2.3 g of triphenylphosphine and 0.27 g of methanol were placed in 30 ml of tetrahydrofuran. The mixture was cooled on an ice bath to 2° C. and 1.6 g of ethyl azodicarboxylate dissolved in 9 ml of tetrahydrofuran was added dropwise.

Workup

  1. additionwas added dropwise

Sources & evidence

ORD record
ord-70b9a7316e8348f29b11c4f69a806619
Source dataset
uspto-grants-1985_07
Patent number
US04526895

Reaction notes

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