Acetic Anhydride → HCID 18958952, compound

HRID 1708561Notes

Reaction equation

HRID 1708561 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH:13]([C:18]#[N:19])[CH2:12]2.[C:20](OC(=O)C)(=O)[CH3:21]>C(O)(=O)C>[C:18]([CH:13]1[CH2:12][C:11]2[C:15](=[CH:16][CH:17]=[C:9]([N:8]3[C:7]4[CH:6]=[CH:5][N:4]=[CH:3][C:2]=4[N:1]=[C:20]3[CH3:21])[CH:10]=2)[CH2:14]1)#[N:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18958969HCID 18958969, compound

Product 1

HCID 18958952HCID 18958952, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-(3-aminopyrid-4-ylamino)-2-cyanoindane (12.28 g, ca 44.5 mmol from step (d) above), acetic acid (70 ml) and acetic anhydride (70 ml) was heated at reflux under nitrogen for 1.75 hours, cooled, and concentrated under reduced pressure. The residual brown gum was dissolved in 2M hydrochloric acid (40 ml) and washed with ethyl acetate (50 ml). The aqueous layer was rendered basic by the addition of 2M aqueous sodium hydroxide, and the product was extracted into dichloromethane. The combined extracts were wahsed with water (50 ml), dried over magnesium sulphate and the solvent evaporated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/methanol (7:1), to give a brown gum, which was recrystallised from ethyl acetate/methanol, to give the 2-cyano-5-(2-methylimidazo[4,5-c]pyrid-1-yl)indane as an off-white powder (9.67 g, 79%), m.p. 174°-176° C. Found: C,74.4; H,5.2; N,20.7. C17H14N4 requires C,74.4; H,5.1; N,20.4%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 1.75 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residual brown gum was dissolved in 2M hydrochloric acid (40 ml)
  6. washwashed with ethyl acetate (50 ml)
  7. additionThe aqueous layer was rendered basic by the addition of 2M aqueous sodium hydroxide
  8. extractionthe product was extracted into dichloromethane
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent evaporated
  11. customThe residue was purified by column chromatography on silica gel
  12. washeluting with ethyl acetate/methanol (7:1)
  13. customto give a brown gum, which
  14. customwas recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-28aa7bc6909f4be1a13d0335f5628d64
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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