Triethylamine → 4-Isocyanato-2-methylquinoline

HRID 2223720Notes

Reaction equation

HRID 2223720 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](C(O)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1>CN(C=O)C>[N:17]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1)=[C:20]=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6044422-methylquinoline-4-carboxylic acid

Product 1

HCID 179565834-Isocyanato-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-methyl-quinoline-4-carboxylic acid (276 mg, 1.2 mmol) in DMF (4 mL) at 0° C. is added triethylamine (1.22 mg, 1.2 mmol) and slowly (30 min) DPPA (332 mg, 1.2 mmol). The reaction mixture is stirred for 2 h at 0° C. and 12 h at 20° C. The reaction is quenched with ice (10 g) and extracted with Et2O (6×30 mL). The combined organic extracts are washed successively with saturated NaHCO3 (2×15 mL) and water (2×10 mL), and are evaporated without heating in vacuo. The residue is dissolved in dry toluene and heated at reflux for 2 h. The resulting solution is carried forward without further isolation of the title compound.

Workup

  1. customThe reaction is quenched with ice (10 g)
  2. extractionextracted with Et2O (6×30 mL)
  3. washThe combined organic extracts are washed successively with saturated NaHCO3 (2×15 mL) and water (2×10 mL)
  4. customare evaporated
  5. temperaturewithout heating in vacuo
  6. dissolutionThe residue is dissolved in dry toluene
  7. temperatureheated
  8. temperatureat reflux for 2 h

Sources & evidence

ORD record
ord-35282b5883d9488ba5d78be14dcd19a0
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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