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

HRID 1678272Notes

Reaction equation

HRID 1678272 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-(5), 744.1 mg, 2.12 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise to the suspension 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-7fb473753d0842f99f25672f3e2b4f26
Source dataset
uspto-grants-2011_08
Patent number
US08008497B2

Reaction notes

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