5-nitro-2-(1H-tetrazol-1-yl)pyridine → 6-(1H-1,2,3,4-tetrazol-1-yl)pyridin-3-amine

HRID 1502168Notes

Reaction equation

HRID 1502168 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[N:8][CH:9]=1)([O-])=O>C(O)(=O)C.CCOC(C)=O.[Zn]>[N:10]1([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:14]=[N:13][N:12]=[N:11]1

Participants

5

Reactant 1

HCID 669272915-nitro-2-(1H-tetrazol-1-yl)pyridine

Product 1

HCID 669273386-(1H-1,2,3,4-tetrazol-1-yl)pyridin-3-amine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

5-Nitro-2-(1H-tetrazol-1-yl)pyridine (1020 mg, 5.31 mmol) was suspended in acetic acid (10 ml). Zinc (3472 mg, 53.1 mmol) was added slowly (exothermic reaction). The mixture was stirred at 50° C. for 1 hour, cooled, diluted with EtOAc. The mixture was filtered, rinsed with ethyl acetate. The filtrate was concentrated to dryness to give crude 6-(1H-tetrazol-1-yl)pyridin-3-amine: LC/MS: [(M+1-28)]+=135.1.9.

Workup

  1. custom(exothermic reaction)
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-54587d0a04e94856ae4a725733cffb33
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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