Diethylamine → HCID 86631098, compound

HRID 870273Notes

Reaction equation

HRID 870273 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[N:15]O)[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C(NCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H][H].[O-]S([O-])(=O)=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.[Cl-].[Na+].O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[CH2:7][C@H:8]1[NH:15][C@H:9]1[C:10]2([CH3:14])[CH3:13]

Participants

10

Reactant 6

HCID 8021DiethylamineHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59925101HCID 59925101, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86631098HCID 86631098, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-napthalen-2-one oxime (15.3 g, 70 mmol) in THF (240 mL) was added diethylamine (18 mL). The reaction mixture was cooled to 0° C. and a 2.0 M solution of lithium aluminum hydride in THF (100 mL, 200 mmol) was added slowly over 20 min to control the rate of hydrogen evolution. The reaction mixture was heated to 70° C. for 1 h, cooled to 0° C. and Na2SO4 10H2O (20 g), brine (60 mL), and EtOAc (300 mL) were added. The solid were washed with EtOAc (4×100 mL); the combined organic layers were washed with water (4×100 mL) and brine (100 mL), dried with Na2SO4, and concentrated to give crude title product (14.3 g). The crude product was dissolved in EtOAc (500 mL), extracted with 0.1 N HCl (100 mL), then with 0.3 N HCl (225 mL). Sodium carbonate (8 g, 75 mmol) was added to the aqueous layer which was extracted with EtOAc (4×200 mL). Organic layers were combined, dried with Na2SO4 and concentrated to give the title compound as an oil (10.1 g) which crystallized on standing to a tan solid. (m/z): [M+H]+ calcd for C13H12NO 204.14; found 204.2.

Workup

  1. temperatureThe reaction mixture was heated to 70° C. for 1 h
  2. temperaturecooled to 0° C.
  3. washThe solid were washed with EtOAc (4×100 mL)
  4. washthe combined organic layers were washed with water (4×100 mL) and brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customto give crude title product (14.3 g)
  8. extractionextracted with 0.1 N HCl (100 mL)
  9. extractionwas extracted with EtOAc (4×200 mL)
  10. dry with materialdried with Na2SO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0624e1d9f68e4b4f88f3b1fe7113c275
Source dataset
uspto-grants-2015_03
Patent number
US08969370B2

Reaction notes

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