2,6-Lutidine → HCID 131718340, compound

HRID 1975855Notes

Reaction equation

HRID 1975855 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[CH:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])[CH3:3].[ClH:24].[O:25]([NH2:27])[CH3:26].N1C(C)=CC=CC=1C>C1COCC1>[ClH:24].[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:8]([NH:27][O:25][CH3:26])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 79372,6-Lutidine2×HCID 521874O-Methylhydroxylamine hydrochloride2×HCID 20088782HCID 20088782, compound

Product 1

HCID 131718340HCID 131718340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Over a 20 minute period a solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxy-α-phenylbenzyl bromide, Example 17, (6.23 g, 0.0166 mole) in 100 mL THF is added to a mixture of methoxylamine hydrochloride (4.18 g, 0.05 mole) and 5.62 g (0.0524 mole) of 2,6 lutidine in 175 mL THF. The reaction mixture is heated under reflux for 16 hours. An additional 5.62 g (0.0524 mole) of 2,6 lutidine and 2.0 g (0.0239 mole) of methoxylamine hydrochloride is added and reflux is continued for 24 hours. The mixture is evaporated to dryness and the residue is taken up in Et2O, washed with H2O, 1N HCl, saturated NaHCO3 and brine. After evaporation to dryness the residue is treated with 5 mL of 20% ethereal HCl (w/v). Creamy white crystals form and are filtered off and recrystallized from EtOAc-Et2O to give an off-white solid, 3.6 g (57 %), m.p. 183°-185° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 16 hours
  3. temperaturereflux
  4. customThe mixture is evaporated to dryness
  5. washwashed with H2O, 1N HCl, saturated NaHCO3 and brine
  6. customAfter evaporation to dryness the residue
  7. additionis treated with 5 mL of 20% ethereal HCl (w/v)
  8. filtrationCreamy white crystals form and are filtered off
  9. customrecrystallized from EtOAc-Et2O
  10. customto give an off-white solid, 3.6 g (57 %), m.p. 183°-185° C.

Sources & evidence

ORD record
ord-e4ae460ed91b44fe9b581f9e85ef11b8
Source dataset
uspto-grants-1994_02
Patent number
US05288896

Reaction notes

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