Hydrochloric Acid → Nitecapone

HRID 1195932Notes

Reaction equation

HRID 1195932 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.[CH3:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18].Cl>O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=[C:16]([C:15](=[O:20])[CH3:14])[C:17](=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 5464105Nitecapone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 1.83 g of 3,4-dihydroxy-5-nitrobenzaldehyde and 1.00 g of 2,4-pentanedione in 10 ml of tetrahydrofuran was saturated with gaseous hydrogen chloride. After standing over night at 5° C. the product was filtered and washed with ether. Yield 1.2 g (50%), m.p. 175°-178° C.

Workup

  1. waitAfter standing over night at 5° C.
  2. filtrationthe product was filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-d8093997f5794b7abcbe30f9d641836a
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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