Ethyl Acetate → 6-methoxy-3-(4-nitro-pyrazol-1-yl)-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene

HRID 1422907Notes

Reaction equation

HRID 1422907 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][CH:15]([N:30]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[N:31]1)[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][C:18]=1[OH:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>CN(C)C=O>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][C:18]1[O:29][CH2:14][CH:15]([N:30]3[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[N:31]3)[CH2:16][C:17]2=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 672477994-[3-Hydroxy-2-(4-nitro-pyrazol-1-yl)-propyl]-6-methoxy-quinolin-3-ol

Product 1

HCID 672482606-methoxy-3-(4-nitro-pyrazol-1-yl)-3,4-dihydro-2H-1-oxa-9-aza-phenanthreneYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethyl azodicarboxylate (250 μL, 1.87 mmol, 6.43 eq) is added at room temperature to a stirred solution of 4-[3-hydroxy-2-(4-nitro-pyrazol-1-yl)-propyl]-6-methoxy-quinolin-3-ol (100 mg, 0.29 mmol, 1.0 eq) and triphenylphosphine (122 mg, 0.46 mmol, 1.6 eq) in N,N-dimethylformamide (38 mL). After 3 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×20 mL) and water (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 1:1, v/v) to afford 6-methoxy-3-(4-nitro-pyrazol-1-yl)-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene as a light yellow solid (60 mg, 63% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×20 mL) and water (20 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-dccb490cb20847dba24961fa97fd9dfe
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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