Hydrochloric Acid → HCID 69045016, compound

HRID 735295Notes

Reaction equation

HRID 735295 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].CC(C)([O-])C.[K+].Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].Cl>CN(C=O)C.C1(C)C=CC=CC=1.CCCCCCC>[NH2:14][C:13]1[C:12]2[C:11](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]([C:8]#[N:9])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:26]=1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8794PhenylacetonitrileHCID 133912-ChlorobenzonitrileHCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 69045016HCID 69045016, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×HCID 8900HeptaneSolvent

Procedure

A mixture of 2-phenylacetonitrile (5.86 g, 50 mmol) and 2-chlorobenzonitrile (7.22 g, 1.05 eq) in DMF (15 mL) was added to a solution of potassium t-butoxide (13.0 g, 2.2 eq, 95%) in DMF (30 mL) cooled with an ice-water bath at a rate such that the internal temperature not exceeding 25° C. 30 min after completion of addition, t-butyl bromoacetate (8.86 mL, 1.2 eq) was added dropwise. The resultant mixture was stirred at room temperature for 24 h, then poured to a mixture of 0.1 N HCl (200 mL), heptane (30 mL) and toluene (15 mL). No solid precipitate was formed. The mixture was extracted with ether (3×150 mL). The combined extracts were washed with water, brine, dried (MgSO4) and concentrated to about 50 mL of total volume to give a precipitate. The solid was collected by filtration, and washed with hexane, and ethyl acetate-hexane mixture (1:1) to give the desired tert-butyl 3-amino-1-cyano-1-phenyl-1H-indene-2-carboxylate (7.65 g, 46%). MS Found: (M+H)+=333.

Workup

  1. temperaturecooled with an ice-water bath at a rate such that the internal temperature not
  2. customexceeding 25° C
  3. additionwas added dropwise
  4. customNo solid precipitate was formed
  5. extractionThe mixture was extracted with ether (3×150 mL)
  6. washThe combined extracts were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated to about 50 mL of total volume
  9. customto give a precipitate
  10. filtrationThe solid was collected by filtration
  11. washwashed with hexane, and ethyl acetate-hexane mixture (1:1)

Sources & evidence

ORD record
ord-85d59cc2177341b4aeb002394d619317
Source dataset
uspto-grants-2009_09
Patent number
US07592461B2

Reaction notes

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