Bromoacetonitrile → HCID 86663252, compound

HRID 2070800Notes

Reaction equation

HRID 2070800 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:14][CH2:15][N:16](C(C)C)C(C)C.BrCC#N>C1COCC1>[C:15]([CH2:14][NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])#[N:16]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 13399999Methyl 3-amino-4-ethylbenzoate

Product 1

HCID 86663252HCID 86663252, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-amino-4-ethylbenzoate (6.10 g) in THF (56.7 mL) at room temperature was added Hunig's Base (11.89 mL) followed by bromoacetonitrile (4.74 mL). The mixture was heated at reflux for 16 h. The reaction was cooled to room temperature and concentrated in vacuo. 1N aqueous HCl and DCM were added. The organic layer was separated, dried (MgSO4) and concentrated to give the subtitle compound as an oil (7.46 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. addition1N aqueous HCl and DCM were added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-86e5ca148c1349a788e6e0182954d060
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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