4-Aminobenzonitrile → 213978-36-0

HRID 1603205Notes

Reaction equation

HRID 1603205 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7]Cl)[C:3](Br)=[O:4].[NH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.[OH-].[Na+]>C(#N)C>[Br:1][CH:2]1[CH2:6][CH2:7][N:9]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 14798Sodium HydroxideHCID 110327461719-99-9

Product 1

HCID 9860086213978-36-0

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo4-chlorobutyryl bromide (BCBB, 145.7 g, 0.540 mole) was added via an addition funnel to a cold (5° C.), well stirred slurry of 4-aminobenzonitrile (4-ABN, 55.0 g, 0.466 mole), Na3PO4 (42 g, 0.256 mole) and acetonitrile (550 mL) in a 1 liter flask while maintaining a temperature below 30° C. during the addition. The addition funnel was rinsed with acetonitrile (55 mL). Upon completion of the coupling (determined by LC), a 50 wt % solution of NaOH (56 mL, 1.061 mole) was added via an addition funnel while maintaining the reaction temperature below 30° C. Upon completion of the reaction (determined by LC), the slurry was filtered through a pressure filter (10 micron polypropylene filter cloth). The flask and the cake were washed with acetonitrile (256 mL). The filtrate and the wash were combined to afford a solution of 4-(3-bromo-2-oxopyrrolidin-1-yl)benzonitrile in acetonitrile (of about 17 wt %). Qualitative LC analysis showed the product with 91.8 to 95 area % purity.

Workup

  1. temperaturewhile maintaining a temperature below 30° C.
  2. additionduring the addition
  3. washThe addition funnel was rinsed with acetonitrile (55 mL)
  4. temperaturewhile maintaining the reaction temperature below 30° C
  5. customUpon completion of the reaction (determined by LC)
  6. filtrationthe slurry was filtered through a pressure
  7. filtrationfilter
  8. filtration(10 micron polypropylene filter cloth)
  9. washThe flask and the cake were washed with acetonitrile (256 mL)

Sources & evidence

ORD record
ord-44bceb09cfc547dea5c4fb221191bf8d
Source dataset
uspto-grants-1999_11
Patent number
US05986107

Reaction notes

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