Ethyl Acetate → HCID 11217334, compound

HRID 1913376Notes

Reaction equation

HRID 1913376 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[N-:8]=[N+:9]=[N-:10].[Na+].[CH:12](OC)(OC)OC.CCOC(C)=O>CC(O)=O>[N:1]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=[N:10][N:9]=[N:8]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9005Trimethyl orthoformateHCID 100093-AminopyridineHCID 33557Sodium Azide

Product 1

HCID 11217334HCID 11217334, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-aminopyridine (1.3 g, 13.4 mmol) in HOAc (20 mL) was added sodium azide (1.3 g, 20.1 mmol) and trimethyl orthoformate (2.36 mL, 21.6 mmol) and the resultant slurry was stirred at room temperature overnight and subsequently refluxed for 6 h. The reaction was cooled to room temperature and stopped by pouring into 50 mL of ice water. EtOAc (50 mL) was added, collected and subsequently washed with aqueous sodium hydroxide (1 N). The organic layer was collected, dried (MgSO4) and concentrated in vacuo to afford the title compound 65 (1.0 g, 52%) as a white solid: mp=74-76° C.; 1H NMR (CDCl3) δ 10.37 (s, 1H), 9.36 (m, 1H), 8.98 (m, 1H), 8.56 (m, 1H), 7.88 (m, 1H); LRMS (ESI) m/z calcd for C6H6N3 [M+H—N2]+ 120. found 120; HRMS (ESI) m/z calcd for C6H6N5 [M+H]+ 148.0623. found 148.0636; HPLC>99% (tR=3.44 min, 60 (A):40 (B): 0.009 (C); tR=2.71 min, 60 (A):40 (B): 0.02 (C)).

Workup

  1. temperaturesubsequently refluxed for 6 h
  2. temperatureThe reaction was cooled to room temperature
  3. customcollected
  4. washsubsequently washed with aqueous sodium hydroxide (1 N)
  5. customThe organic layer was collected
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-def0293419144e1f91134d221a49db14
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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