Methane → HCID 19867084, compound

HRID 1904358Notes

Reaction equation

HRID 1904358 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[CH:4][C:3]=1/[CH:14]=[CH:15]/[C:16]([O:18]CC)=O.C>C(O)C.C1(C)C(C)=CC=CC=1>[CH3:8][C:7]1[CH:6]=[C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)[CH:4]=[C:3]2[C:2]=1[NH:1][C:16](=[O:18])[CH2:15][CH2:14]2

Participants

5

Reactant 2

HCID 297MethaneHCID 86742011HCID 86742011, compound

Product 1

HCID 19867084HCID 19867084, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7237O-XyleneSolvent

Procedure

A suspension of trans-ethyl 3-(2-amino-3-methyl-5-[tetrazol1-yl]phenyl)prop-2-enoate (2.5 g) in ethanol (250 cm3) was hydrogenated at 60° and 15 p.s.i. (1.04×105Pa) pressure over 10% palladised charcoal (1 g) for 11/2 hours. The cooled mixture was filtered through "Solkafloc" (Trade Mark) and evaporated in vacuo to afford a solid. A suspension of this solid in xylene (100 cm3) was heated under reflux for 7 hours. The mixture was then cooled and the product filtered off and washed with dichloromethane:methanol, 5:1, to afford 3,4-dihydro-8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone, m.p. 271°-272°, (1.37 g).

Workup

  1. customwas hydrogenated at 60°
  2. custom2 hours
  3. filtrationThe cooled mixture was filtered through "Solkafloc" (Trade Mark)
  4. customevaporated in vacuo
  5. customto afford a solid
  6. temperaturewas heated
  7. temperatureunder reflux for 7 hours
  8. temperatureThe mixture was then cooled
  9. filtrationthe product filtered off
  10. washwashed with dichloromethane

Sources & evidence

ORD record
ord-a555e40e27ab48a58cc9a965ec875013
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

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