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Triphenylphosphine → 3-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline

HRID 1829928
Notes
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Reaction equation

HRID 1829928 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14](O)=[C:13]([Cl:18])[CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:18][C:13]1[CH:12]=[C:11]([NH2:10])[CH:16]=[CH:15][C:14]=1[O:9][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 707366-Methyl-2-pyridylmethanolHCID 775784-Amino-2-chlorophenolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 220552383-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixture of (6-methyl-pyridin-2-yl)-methanol (280 mg, 2.29 mmol), 4-amino-2-chloro-phenol (359 mg, 2.5 mmol) and triphenylphosphine (0.655 mg, 2.5 mmol) in THF (8 ml) was added DIAD (0.49 ml, 2.5 mmol) and the mixture was stirred at rt for 20 h. The mixture was concentrated in vacuo, diluted with 1N HCl (30 ml), washed with EtOAc (3×20 ml) and basified to pH 12 by 1N NaOH. The mixture was extracted with EtOAc (4×40 ml); the combined EtOAc extracts were washed with brine (1×20 ml), dried (MgSO4), filtered and concentrated in vacuo to give 15A (?? mg, ??% pure)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with 1N HCl (30 ml)
  3. washwashed with EtOAc (3×20 ml)
  4. extractionThe mixture was extracted with EtOAc (4×40 ml)
  5. washthe combined EtOAc extracts were washed with brine (1×20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b298dfc11e964586aa31546be83e2eb2
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07064203B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes