HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25781
Notes
Print preview

Reaction equation

HRID 25781 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[CH3:21].[Li]CCCC.[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28].O>C(Cl)Cl.CCCCCC>[C:27]([O:31][C:32]([N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[CH:18][CH:17]=2)[C:12]([CH3:21])=[CH:13][C:14]1([CH3:20])[CH3:19])=[O:33])([CH3:30])([CH3:29])[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 225665156-(2-Methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineHCID 178418339Butyllithium

Product 1

HCID 207603346-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl esterYield 42.9%

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 2.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (see Example 1) in 35 mL of CH2Cl2 was cooled down to −78° C. To this mixture, 13.1 mL of 1.6 M n-BuLi in hexane was added dropwise. The mixture was warmed to 0° C. and 2.9 g of (di-tert-butyl)carbonate was added. The mixture was allowed to stir at 0° C. for 1 hour. The reaction was then worked up by adding water and extracting with EtOAc three times. The organic layers were combined, washed sequentially with 1 N HCl, water, saturated aqueous sodium bicarbonate solution, water, saturated aqueous NaCl solution, dried over magnesium sulfate, and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield 1.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

Workup

  1. temperatureThe mixture was warmed to 0° C.
  2. extractionextracting with EtOAc three times
  3. washwashed sequentially with 1 N HCl, water, saturated aqueous sodium bicarbonate solution, water, saturated aqueous NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1f8bf4aae3f14dbab3f2ec3865b2b222
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858627B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes