Pyridine → HCID 59678694, compound

HRID 1751846Notes

Reaction equation

HRID 1751846 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[CH:4]=[O:5].[CH3:14][C:15]([CH3:19])=[CH:16][CH:17]=O.N1C=CC=CC=1>>[OH:1][C:2]1[C:3]([CH:4]=[O:5])=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[C:8]2[C:9]=1[CH:17]=[CH:16][C:15]([CH3:19])([CH3:14])[O:10]2

Participants

4

Reactant 3

HCID 1049PyridineHCID 610203-Methyl-2-butenalHCID 59678646Benzaldehyde, 2,4-dihydroxy-6-nitro-

Product 1

HCID 59678694HCID 59678694, compound

Procedure

A solution of 2,4-dihydroxy-6-nitro-benzaldehyde (10.61 g, 58 mmol) in Me2CO (6 mL) is added during a 5.5 h period to a stirring solution of 3-methyl-but-2-enal (4.00 g, 29 mmol) in pyridine (2.29 g, 2.34 mL, 29 mmol) at 120° C. After completion of addition heating is continued for an additional 18 h. The Me2CO is evaporated and the pyridine is removed by azeotrope distillation with toluene to afford a crude product. The crude product is purified using silica gel chromatography with 1% ethyl acetate in hexanes to afford 5-hydroxy-2,2-dimethyl-7-nitro-2H-chromene-6-carbaldehyde.

Workup

  1. additionAfter completion of addition
  2. temperatureheating
  3. customThe Me2CO is evaporated
  4. customthe pyridine is removed by azeotrope distillation with toluene
  5. customto afford a crude product
  6. customThe crude product is purified

Sources & evidence

ORD record
ord-4a76bccbf31347baaf876339f877187f
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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