Sodium Carbonate → HCID 14450299, compound

HRID 568368Notes

Reaction equation

HRID 568368 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[N:13]=[N:12][CH:11]=[N:10]2)=[CH:4][C:3]=1/[CH:14]=[CH:15]/[C:16]([O:18]CC)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH3:8][C:7]1[CH:6]=[C:5]([N:9]2[N:13]=[N:12][CH:11]=[N:10]2)[CH:4]=[C:3]2[C:2]=1[NH:1][C:16](=[O:18])[CH:15]=[CH:14]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 14450290HCID 14450290, compound

Product 1

HCID 14450299HCID 14450299, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5M Hydrochloric acid (20 cm3) was added to trans-ethyl 3-(2-amino-3-methyl-5-[tetrazol-2-yl]phenyl)prop-2-enoate (0.45 g) and the mixture was heated on a steam bath for 1 hour. The mixture was then cooled, brought to pH 7 with aqueous sodium carbonate solution, and extracted with dichloromethane:methanol, 20:1 (3×50 cm3). The combined organic extracts were dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl/acetate:methanol, 10:1. Combination and evaporation of the appropriate fractions afforded 8-methyl-6-(tetrazol-2-yl)-2-(1H)-quinolone, 0.25H2O, m.p. 264°-266°, (0.08 g).

Workup

  1. temperaturethe mixture was heated on a steam bath for 1 hour
  2. temperatureThe mixture was then cooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with ethyl/acetate
  9. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-2e9a215880b44f15aedec11911a8f7f2
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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