Triethylamine → 5-Hydroxyquinoline-2-carbonitrile

HRID 1822677

Reaction equation

HRID 1822677 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)#[N:2].C[Si](C#N)(C)C.[OH:19]C1C=CC=C2C=1C=CC=[N+]2[O-].C(N(CC)CC)C>CC#N>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:19])[N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 74031Quinoline-2-carbonitrileHCID 82115Trimethylsilyl cyanideHCID 178526244HCID 178526244, compound

Product 1

HCID 1357436975-Hydroxyquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Typical procedure to prepare 2-cyanoquinoline from N-oxide: Preparation of 2-cyano-5-hydroxyl-2-quinoline: Trimethylsilyl cyanide (12.4 ml) was added into a solution of 5-hydroxyl-quinoline N-oxide (5 g) with triethylamine (13 ml) in MeCN. After the reaction was stirred at room temperature for 12 hours, solvents were removed under vaccum to provide a residue which was then partitioned between saturated NaHCO3 solution (100 ml) and EtOAc (100 ml). The aqueous solution was then extracted with EtOAc (2×100 ml). And the combined organic layer was dried over anhydrous MgSO4, filtered and concentrated to afford a crude product which purified by silica gel column chromatography to provide 5.3 g of 2-cyano-5-hydroxylquinoline. MS m/z: (M+H)+ calcd for C10H7N2O 171.06, found 171.03. HPLC retention time: 1.22 minutes (column I).

Workup

  1. customsolvents were removed under vaccum
  2. customto provide a residue which
  3. customwas then partitioned between saturated NaHCO3 solution (100 ml) and EtOAc (100 ml)
  4. extractionThe aqueous solution was then extracted with EtOAc (2×100 ml)
  5. dry with materialAnd the combined organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a crude product which
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c22a015259ca436997e01b9574af9cee
Source dataset
uspto-grants-2006_05
Patent number
US07037913B2

Linked notes

Loading…