Isopropanol → HCID 135964999, compound

HRID 1974681Notes

Reaction equation

HRID 1974681 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.[N:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.C(O)(C)C>C(OC(=O)C)(=O)C>[N+:11]([C:8]1[CH:7]=[C:4]([CH:5]=[CH:20][C:17]2[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=2)[CH:3]=[C:2]([OH:1])[C:9]=1[OH:10])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 79634-MethylpyridineHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 135964999HCID 135964999, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution containing 2.0 g (0.011 mole) of 3,4-dihydroxy-5-nitrobenzaldehyde and 2.23 g (0.024 mole) of 4-picoline in 9.0 ml of acetic anhydride was refluxed for 1 h. About 15 ml of isopropanol was then added and the solution was cooled to 0° C. where upon the diacetyl-derivative of the desired product crystallized. After filtration the product was suspended in 100 ml of 0.5N hydrochloric acid and refluxed for 1.5 h. After cooling the precipitate was filtered, washed with water and acetone and dried. Yield 1.89 g (67%), m.p. above 350° C.

Workup

  1. temperaturewas refluxed for 1 h

Sources & evidence

ORD record
ord-277b1c50519e4fd5a1b42f8ef1fdadc8
Source dataset
uspto-grants-1994_02
Patent number
US05283352

Reaction notes

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