Formaldehyde → HCID 10108827, compound

HRID 1813916Notes

Reaction equation

HRID 1813916 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[CH2:24][OH:25])[CH2:4][CH3:5])[CH3:2].C=O.[CH3:28]C1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[C:8]=1[CH2:24][O:25][CH2:28][N:14]2[C:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[CH3:21])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 21912329HCID 21912329, compound

Product 1

HCID 10108827HCID 10108827, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of [4-(1-ethyl-propoxy)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-pyridin-3-yl]-methanol (79 mg, 0.231 mmol), 37% aqueous formaldehyde (0.1 ml) and p-TsOH (22 mg, 0.116 mmol) in 10 ml of toluene was heated at reflux using a Dean-Stark apparatus for 3 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 100 mg of the crude material. The crude material was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give 40 mg (50%) of the title compound as a clear oil. 1H NMR (CDCl3) δ 6.90(s,2H), 6.04(s,1H), 4.87(2 sets of s, 4H), 4.16(m,1H), 2.28(s,3H), 2.19(s,3H), 2.14(s,6H), 1.67(m,4H), 0.94(t,6H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 3 hours
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated
  9. customto give 100 mg of the crude material
  10. customThe crude material was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-85941fc3e024437293d1c93710355be0
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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