Methanol → HCID 68549576, compound

HRID 2359838Notes

Reaction equation

HRID 2359838 reaction equation
[NH2:1][C:2]1[C:11]([CH2:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[OH:21])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.C(OC(N=NC(OC(C)C)=O)=O)(C)C>C1COCC1.O>[CH3:20][O:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([O:21][CH3:22])[C:13]=1[CH2:12][C:11]1[C:2]([NH2:1])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68547606HCID 68547606, compound

Product 1

HCID 68549576HCID 68549576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-[(2-Aminoquinolin-3-yl)methyl]-3-methoxyphenol (40 mg, 0.14 mmol), triphenylphosphine (56 mg, 0.21 mmol) and methanol (7 μL, 0.22 mmol) were placed in THF (2 mL) at 10° C. and then mixed slowly with azodicarboxylate diisopropyl ester (44 mg, 0.22 mmol) in THF (1 mL). Then the mixture was stirred for 12 hours at room temperature. The batch was mixed with water and extracted with ethyl acetate. The combined organic phases were washed with water, dried (sodium sulfate) and concentrated. The crude product was purified chromatographically (silica gel, dichloromethane, methanol). To remove traces of triphenylphosphine oxide, the slightly contaminated product was dissolved in diethyl ether and extracted with 2N aqueous hydrochloric acid. The aqueous phase was alkalized with dilute sodium hydroxide solution and extracted with dichloromethane. The combined dichloromethane extracts were washed with water until neutral, dried (sodium sulfate) and concentrated (yield: 5 mg, 9%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe crude product was purified chromatographically (silica gel, dichloromethane, methanol)
  6. customTo remove traces of triphenylphosphine oxide
  7. dissolutionthe slightly contaminated product was dissolved in diethyl ether
  8. extractionextracted with 2N aqueous hydrochloric acid
  9. extractionextracted with dichloromethane
  10. washThe combined dichloromethane extracts were washed with water until neutral,
  11. dry with materialdried (sodium sulfate)
  12. concentrationconcentrated (yield: 5 mg, 9%)

Sources & evidence

ORD record
ord-e104723b02464308ae92ae9333d06c83
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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