Hydrochloric Acid → 6-(2-Hydroxy-4-methoxymethoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1968462Notes

Reaction equation

HRID 1968462 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:26](=[CH:27][CH:28]=1)[C:25]1[C:16](=[C:17]3[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:30])([CH3:29])[CH:19]=[C:18]3[CH3:31])[C:15](=[O:32])[O:14]2.Cl>O1CCCC1.C(OCC)(=O)C.O>[OH:14][C:13]1[CH:12]=[C:11]([O:10][CH2:9][O:8][CH3:7])[CH:28]=[CH:27][C:26]=1[C:25]1[C:16]([CH2:15][OH:32])=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:30])([CH3:29])[CH:19]=[C:18]2[CH3:31]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 579906038-Methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one

Product 1

HCID 579906086-(2-Hydroxy-4-methoxymethoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Lithium aluminum hydride (167 mg, 4.40 mmol) was suspended in anhydrous tetrahydrofuran (3 mL). A solution of 8-methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-1-(5), 744.1 mg, 2.12 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise at 0° C., the reaction mixture was stirred at the same temperature for 30 minutes. Ethyl acetate (2 mL) and water (1 mL) were added to the reaction mixture successively, and then ethyl acetate (150 mL) was added thereto. 1N aqueous HCl solution (6 mL) was added, the mixture was washed with water (100 mL, twice) and saturated brine (50 mL) successively, and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the titled reference compound (750.6 mg) as a pale yellow amorphous product. (Quantitative)

Workup

  1. washthe mixture was washed with water (100 mL
  2. dry with materialtwice) and saturated brine (50 mL) successively, and then dried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dfe1025e87c54451852f6276c9c551eb
Source dataset
uspto-grants-2013_04
Patent number
US08426406B2

Reaction notes

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