2,6-Dimethylaniline → Glycine, N-(2,6-dimethylphenyl)-

HRID 553357Notes

Reaction equation

HRID 553357 reaction equation
CC1C=CC=C(C)C=1N.BrCC(OCC)=O.Br.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[NH:26][CH2:27][C:28]([OH:30])=[O:29]>ClCCl>[CH3:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([CH3:18])[C:20]=1[NH:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 7748Ethyl bromoacetateHCID 21879725HCID 21879725, compound

Product 1

HCID 826274Glycine, N-(2,6-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dimethylaniline (6.1 g, 50.4 mmol), and ethyl bromoacetate (8.4 g, 50.4 mmol) were refluxed neat for 10 min. The reaction mixture was cooled to room temperature and poured into dichloromethane (75 mL). A precipitated formed which was collected and triturated with dichloromethane (25 mL). N-(2,6-Dimethylphenyl)glycine hydrobromide salt (1.21 g, 4.6 mmol, 9.0%) was collected as a white crystalline solid. 1H NMR (CD3OD) d 2.48 (s, 6H), 4.29 (s, 2H), 7.00-7.10 (m, 3H).

Workup

  1. customA precipitated
  2. customformed which
  3. customwas collected
  4. customtriturated with dichloromethane (25 mL)

Sources & evidence

ORD record
ord-73eedfa891fa4f6d9a6f0fc3572d1a00
Source dataset
uspto-grants-2011_11
Patent number
USRE042889E1

Reaction notes

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