Hydrazine hydrate (1:1) → Imidazo[1,2-a]pyridine-7-carbohydrazide

HRID 2400359Notes

Reaction equation

HRID 2400359 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11](I)=[CH:12][N:13]=[C:7]2[CH:6]=1)=O.O.[NH2:16][NH2:17]>C(O)C>[N:13]1[CH:12]=[CH:11][N:8]2[CH:9]=[CH:10][C:5]([C:3]([NH:16][NH2:17])=[O:2])=[CH:6][C:7]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57497695Methyl 3-iodoimidazo(1,2-a)pyridine-7-carboxylate

Product 1

HCID 55281632Imidazo[1,2-a]pyridine-7-carbohydrazideYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl-3-Iodo-imidazo[1,2-a]pyridine-7-carboxylate (0.3 g, 1.7 mmol, 1.0 equiv) in ethanol (3 ml) was added hydrazine hydrate (0.414 ml, 8.52 mmol). The mixture was heated to 70 deg C. for 1 h then allowed to cool. The solid was filtered off and washed with ethyl acetate and ether then dried to afford 0.209 g of product. 1H NMR (400 MHz, DMSO-d6): 9.95 (1H, s), 8.60 (1H, d), 8.05 (2H, d), 7.70 (1H, d), 7.30 (1H, dd), 4.58 (2H, s).

Workup

  1. temperatureThe mixture was heated to 70 deg C
  2. temperatureto cool
  3. filtrationThe solid was filtered off
  4. washwashed with ethyl acetate and ether
  5. customthen dried

Sources & evidence

ORD record
ord-12641d9e9b1548499dd0abdc11e32809
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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