O-Methylhydroxylamine hydrochloride → HCID 72448476, compound

HRID 1623202Notes

Reaction equation

HRID 1623202 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].CO[CH:7](OC)[CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:24])[C:14]=2[N:13]=[C:12]1[CH3:25]>C(O)C>[CH3:3][O:2][N:4]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:24])[C:14]=2[N:13]=[C:12]1[CH3:25]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69507348HCID 69507348, compound

Product 1

HCID 72448476HCID 72448476, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methoxylamine hydrochloride (22.8 g, 272 mmol) was added to a solution of 1-(4,4-dimethoxybutyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (36.6 g, 136 mmol) in ethanol (200 mL). The reaction mixture was stirred at room temperature for two hours, then was concentrated under reduced pressure. The residue was diluted with water and brought to pH 7 with saturated aqueous sodium bicarbonate. The mixture was extracted with 5% methanol/dichloromethane. The organic layers were combined, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, elution with 5% methanol in dichloromethane) followed by recrystallization from ethyl acetate to yield 4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal O-methyloxime as an off-white powder, mp 153-155° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionThe mixture was extracted with 5% methanol/dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (silica gel, elution with 5% methanol in dichloromethane)
  9. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0eb5e12f38144eeeb1ce8068f592d9c0
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

Loading…