Ammonia → HCID 10399247, compound

HRID 617291Notes

Reaction equation

HRID 617291 reaction equation
C(OC([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=O)(C)(C)C.[ClH:20].C(OCC)C.N>C(O)C.O>[ClH:20].[ClH:20].[NH:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 10801571HCID 10801571, compound

Product 1

HCID 10399247HCID 10399247, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To an ice cooled solution of the compound of step 9a (286 mg, 1.08 mmol) in absolute ethanol (4 mL), was added a hydrogen chloride saturated ethanol solution (4 mL), under nitrogen. The reaction mixture was stirred 18 hours while gradually warming to room temperature. The reaction mixture was then concentrated in vacuo, the product dissolved in absolute ethanol and triturated with diethyl ether. Two recrystallizations from ethanol and diethyl ether yielded pure product in 81% yield as a white powder (174 mg, 87 mmol). MS (DCI/NH3) m/e 165 (M+H)+, 182 (M+NH4)+. 1NMR (D2O, 300 MHz) δ: 8.60-8.59 (d, J=2.9 Hz, 1H), 8.48-8.46 (d, J=5.8 Hz, 1H), 8.25-8.21 (ddd, J=9.0 Hz, J=2.6 Hz, J=1.1 Hz, 1H), 5.05-4.97 (m, 1H), 4.59-4.57 (d, J=4.0 Hz, 2H), 4.22-4.05 (m, 2H), 2.77-2.67 (dd, J=16.9 Hz, J=8.45 Hz, 2H). Anal. calcd. for C9H12N2O.2.7 HCl.0.2 H2O: C, 40.60; H, 5.71; N, 10.52. Found: C, 40.75; H, 5.76; N, 10.51.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe product dissolved in absolute ethanol
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-4958efa227c641fb98c2a8bcd50348f1
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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