HCID 21460675, compound → HCID 21460686, compound

HRID 2396334Notes

Reaction equation

HRID 2396334 reaction equation
[C:1]([CH2:6][NH:7][C:8]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11])([O:3][CH2:4][CH3:5])=[O:2].CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[NH2:11][C:10]1[C:9]2[C:8](=[CH:15][C:14]([F:16])=[CH:13][CH:12]=2)[NH:7][C:6]=1[C:1]([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 21460675HCID 21460675, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21460686HCID 21460686, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-(Carbethoxy)methylamino-4-fluorobenzonitrile (220 mg, 1 mmol) intetrahydrofuran (3 mL) and add dropwise with stirring to a solution of potassium tert-butoxide (1 mL of a 1M solution in 1 mL tetrahydrofuran) under a nitrogen atmosphere. After 1 hour, dilute with ethyl acetate, rinse with water, dry the organic phase and concentrate in vacuo to yield the title compound (170 mg, 77%).

Workup

  1. additionadd dropwise
  2. washrinse with water
  3. customdry the organic phase
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0f19c3c9270c4a81984dd1f3862aeb6f
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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