Hydrochloric Acid → [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol

HRID 2120988Notes

Reaction equation

HRID 2120988 reaction equation
C([O:8][CH2:9][CH:10]1[O:23][C:14]2=[C:15]3[C:20](=[CH:21][CH:22]=[C:13]2[O:12][CH2:11]1)[N:19]=[CH:18][CH:17]=[CH:16]3)C1C=CC=CC=1.Cl.[C:25]1(C)C=CC=CC=1>>[CH3:25][C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]3[O:12][CH2:11][C@H:10]([CH2:9][OH:8])[O:23][C:14]3=2)[N:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 131724340(Benzyloxy)methyl-2,3-dihydro[1,4]dioxino [2,3-f]-quinoline

Product 1

HCID 11183845[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanolYield 61.9%

Conditions

Temperature
80 °C

Procedure

A mixture of crude (2S)-2[(benzyloxy)methyl-2,3-dihydro[1,4]dioxino [2,3-f]-quinoline product mixture (57.6 g, 0.179 mol) from example 7 in toluene (300 mL) was mixed with 20% HCl (436 g, 3.59 mol) and heated at 80° C. After 30 min, the reaction mixture was cooled to room temperature. The two layers were separated. A 30% NH4OH solution (400 mL) was added to the aqueous layer at 10-20° C. to pH 10. This was stirred for 30 min, the solid was filtered, washed with water and recrystallized from CH3OH (200 mL) to give 25.7 g (61.9%) of the title alcohol as an off-white solid.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe two layers were separated
  3. additionA 30% NH4OH solution (400 mL) was added to the aqueous layer at 10-20° C. to pH 10
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customrecrystallized from CH3OH (200 mL)

Sources & evidence

ORD record
ord-33d1f93590504cfa828b0078b1fe5c31
Source dataset
uspto-grants-2004_02
Patent number
US06693197B2

Reaction notes

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