Hydrochloric Acid → 5-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 909307Notes

Reaction equation

HRID 909307 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:28])[CH:25]=[C:24]([CH3:26])[C:23]2[C:10](=[CH:11][CH:12]=[C:13]3[C:22]=2[C:21](=[O:27])[O:20][C:19]2[C:14]3=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:9]1.C(OCC)(=O)C.Cl>O1CCCC1.O>[OH:27][CH2:21][C:22]1[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[OH:20])=[CH:12][CH:11]=[C:10]2[C:23]=1[C:24]([CH3:26])=[CH:25][C:8]([CH3:28])([CH3:7])[NH:9]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 104937872,2,4-Trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 579906105-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, lithium aluminum hydride (1.48 g, 39.0 mmol) was suspended in anhydrous tetrahydrofuran (30 mL). A solution of 2,2,4-Trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-1, 3.80 g, 13.0 mmol) in anhydrous tetrahydrofuran (40 mL) was added dropwise at 0° C. and the reaction mixture was stirred at the same temperature for 1 hour. Ethyl acetate (15 mL) and water (5 mL) were added dropwise successively to the reaction mixture and then 0.2 N aqueous HCl solution (350 mL) was added thereto. The whole was extracted with ethyl acetate (300 mL, 100 mL). The combined organic layer was washed with water (300 mL) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the titled reference compound (4.01 g) as a pale brown solid. (Yield quantitative)

Workup

  1. extractionThe whole was extracted with ethyl acetate (300 mL, 100 mL)
  2. washThe combined organic layer was washed with water (300 mL) and saturated brine (100 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-48cd91b92307441fbece6f438d52d4ca
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

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