tert-Butanol → HCID 22318072, compound

HRID 1520161Notes

Reaction equation

HRID 1520161 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7](C(O)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([N:16]([CH2:19]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])=CC=1.[CH3:38][C:39]([OH:42])([CH3:41])[CH3:40]>C1(C)C=CC=CC=1.O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:16][C:19](=[O:28])[O:42][C:39]([CH3:41])([CH3:40])[CH3:38])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 825716-Quinolinecarboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 22318072HCID 22318072, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of quinoline-6-carboxylic acid (5 g, 28.87 mmol) in toluene (250 ml) was added triethylamine (14.6 g, 144.28 mmol), DPPA (15.9 g, 57.78 mmol,) with stirring for 1 h at 0° C. in water/ice bath. Then 2-methylpropan-2-ol (6.4 g, 86.34 mmol) was added with stirring overnight at 90° C. in an oil bath and then diluted with water (300 ml), extracted with dichloromethane (3×100 ml), dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether to afford tert-butyl N-(quinolin-6-yl)carbamate as a yellow solid (1.3 g, 18%).

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-b1d6d2d2c9a8493bbf3246ea7655a474
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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