Ethyl Acetate → HCID 53942973, compound

HRID 2165455Notes

Reaction equation

HRID 2165455 reaction equation
[N:1]1([CH2:7][CH:8]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N:18]([O-])=[O:19].[Na+].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>Cl.O>[N:1]1([CH2:7][CH:8]2[N:13]([N:18]=[O:19])[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10][CH2:9]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 6506973-[(Morpholin-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazineHCID 23668193Sodium Nitrite

Product 1

HCID 53942973HCID 53942973, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (-)-3-(4-morpholinylmethyl)-3,4-dihydro-2H-1,4-benzoxazine in 250 ml of 2N aqueous hydrochloric acid was cooled to 0° C. and treated with a solution of 4.8 g (0.070 mole) of sodium nitrite in 50 ml of water. The solution was stirred for one hour at 0° C., poured into a mixture of 1500 ml of water and 1 liter of ethyl acetate and neutralized carefully by the addition of solid sodium bicarbonate. The organic layer was separated, and the aqueous layer was extracted with an additional 400 ml of ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and taken to dryness to give (-)-3-(4-morpholinylmethyl)-4-nitroso-3,4-dihydro-2H-1,4-benzoxazine, which was used as such in the next synthetic step without further purification or characterization.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with an additional 400 ml of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ab32decf27764f69bc0884a1a6b3e7cc
Source dataset
uspto-grants-1990_07
Patent number
US04939138

Reaction notes

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