2-Methoxyaniline → HCID 11000238, compound

HRID 1292839Notes

Reaction equation

HRID 1292839 reaction equation
[CH3:1][C:2]([O:5][C:6]([O:8]C(OC(C)(C)C)=O)=O)(C)C.[CH3:16][O:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20].[Br:25]CCO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:25][CH2:1][CH2:2][O:5][C:6](=[O:8])[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[O:17][CH3:16]

Participants

6

Reactant 3

HCID 70002-MethoxyanilineHCID 108982-BromoethanolHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 11000238HCID 11000238, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent4×

Procedure

In a 50 ml two-necked flask placed under an argon atmosphere, 1.5 g (7 mmol, 1.4 eq) of (Boc)2O is dissolved in 5 ml of anhydrous CH2Cl2. 61 mg (0.5 mol, 10% eq) of DMAP dissolved in 5 ml of anhydrous CH2Cl2 is added, then 0.56 ml (5 mmol) of 2-methoxyaniline is added dropwise. The mixture is stirred at room temperature for 20 min before adding 0.5 ml (7 mmol, 1.4 eq) of 2-bromoethanol diluted in 5 ml of anhydrous CH2Cl2. The reaction is allowed to progress for 30 min at room temperature then for approximately 20 hours under reflux of dichlormethane. Then, the medium is cooled and concentrated under vacuum. The resulting dark pink solid is purified by chromatography on a silica gel column (eluent CH2Cl2) to give 1.33 g of a colorless oil (yield: 95%).

Workup

  1. customIn a 50 ml two-necked flask placed under an argon atmosphere
  2. additionis added
  3. waitto progress for 30 min at room temperature
  4. temperatureThen, the medium is cooled
  5. concentrationconcentrated under vacuum
  6. customThe resulting dark pink solid is purified by chromatography on a silica gel column (eluent CH2Cl2)

Sources & evidence

ORD record
ord-ccc5589c443147e0b330f97d6f1deb26
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

Loading…