Hydrochloric Acid → HCID 14302388, compound

HRID 1200249Notes

Reaction equation

HRID 1200249 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[N:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)([O-])=O.Cl.[OH-].[NH4+].C(OCC)(=O)C.CCCCCC>O.C(OCC)(=O)C>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[N:18][C:9]=1[CH2:8][O:7][C:6]1[CH:5]=[C:4]([NH2:1])[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 14302386HCID 14302386, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 14302388HCID 14302388, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 10 g (0.036 mol) of 2-[(3-nitrophenoxy)methyl]-quinazoline in a solution of 105 g (0.38 mol) of ferrous sulfate heptahydrate and 0.5 ml of concentrated hydrochloric acid in 175 ml of water is heated on a steam bath to 90° C. Concentrated ammonium hydroxide is added in increments of 25 ml, and 3×10 ml over a period of 15 minutes. Heating is discontinued and the reaction mixture is allowed to cool over a period of 45 minutes while vigorously stirring. The reaction mixture is diluted with 500 ml of water/500 ml of ethyl acetate and filtered through Celite. The layers are separated and the ethyl acetate solution is charcoaled, filtered and concentrated to obtain an oil, which is subjected to high pressure liquid chromatography (ethyl acetate/hexane as eluent). Fractions 14-20 are combined and concentrated to obtain 5 g (56%) of off-white crystals, m.p. 103°-7° C.

Workup

  1. temperatureHeating
  2. temperatureto cool over a period of 45 minutes
  3. filtrationfiltered through Celite
  4. customThe layers are separated
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain an oil, which
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f8981ebabc2c45ddb9c3e55f3b2a13d5
Source dataset
uspto-grants-1990_02
Patent number
US04904786

Reaction notes

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