2,4-Diamino-6-methylphenol → HCID 66978002, compound

HRID 1846443Notes

Reaction equation

HRID 1846443 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[CH2:11](C(CC)(CC)C([O-])([O-])[O-])[CH3:12]>C(O)(=O)C>[CH3:11][C:12]1[O:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([NH2:8])=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 275202,4-Diamino-6-methylphenolHCID 21875354Triethylorthoaceate

Product 1

HCID 66978002HCID 66978002, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.00 g (7.20 mmol) 2,4-diamino-6-methyl-phenol, 5.00 mL acetic acid and 15.0 mL (81.8 mmol) triethylorthoacetate were combined and refluxed. The reaction mixture was cooled to RT overnight and evaporated down. The residue was extracted with 0.5 N sodium hydroxide solution and EtOAc and the organic phase was evaporated down. The flask residue was triturated with diethyl ether and the precipitate formed was suction filtered. The mother liquor was evaporated down and the residue was purified by flash chromatography. The product-containing fractions were combined and evaporated down.

Workup

  1. temperaturerefluxed
  2. customevaporated down
  3. extractionThe residue was extracted with 0.5 N sodium hydroxide solution and EtOAc
  4. customthe organic phase was evaporated down
  5. customThe flask residue was triturated with diethyl ether
  6. customthe precipitate formed
  7. filtrationfiltered
  8. customThe mother liquor was evaporated down
  9. customthe residue was purified by flash chromatography
  10. customevaporated down

Sources & evidence

ORD record
ord-516683c0f34f4439a5303ec7c299700e
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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