Hydrogen chloride-ethyl acetate → 10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl cyanide Hydrochloride

HRID 10100Notes

Reaction equation

HRID 10100 reaction equation
C(OC([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[CH:13][C:14]([C:20]#[N:21])=[CH:15][C:16]=32)[CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.[ClH:28]>>[ClH:28].[CH:17]12[CH2:19][CH:10]([CH2:9][NH:8][CH2:18]1)[C:11]1[CH:12]=[CH:13][C:14]([C:20]#[N:21])=[CH:15][C:16]2=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 538637034-Cyano-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester

Product 1

HCID 2186471410-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl cyanide Hydrochloride

Procedure

4-Cyano-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester was treated with 3N HCl ethyl acetate (6 mL) and warmed to reflux for 2 hours, then concentrated, dissolved in a minimum of methanol which was saturated with Et2O and stirred 18 hours. The product was collected by filtration (49 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ 9.66 (br s, NH), 7.86 (br s, NH), 7.74–7.70 (m, 2H), 7.49 (d, J=7.5 Hz, 1H), 3.33–2.97 (m, 6H), 2.17 (m, 1H), 2.01 (d, J=11.0 Hz, 1H). GCMS m/e 184 (M+). M.p. 268–273° C.

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. dissolutiondissolved in a minimum of methanol which
  5. filtrationThe product was collected by filtration (49 mg, 73%)

Sources & evidence

ORD record
ord-6a5a32196acf4e768cde31de4aed7d60
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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