Hydrazine hydrate (1:1) → HCID 86673555, compound

HRID 535481Notes

Reaction equation

HRID 535481 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10](OCC)=[O:11])=O)=[CH:4][N:3]=1.O.[NH2:22][NH2:23]>C(O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[C:8]3[C:9](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10](=[O:11])[NH:23][N:22]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 24723339Ethyl 2-(6-chloropyridine-3-carbonyl)benzoate

Product 1

HCID 86673555HCID 86673555, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of ethyl 2-(6-chloronicotinoyl)benzoate (0.599 g, 2.1 mmol) and hydrazine hydrate (0.35 mL, 6.2 mmol) in ethanol (6 mL) was stirred at 75° C. for 1 hour, concentrated, and azeotroped with toluene to provide the title compound, which was used without purification: 1H NMR (300 MHz, DMSO-d6) δ 13.01 (s, 1H), 8.65 (dd, J=2.7, 0.6, 1H), 8.44-8.25 (m, 1H), 8.13 (dd, J=8.3, 2.5, 1H), 8.08-7.82 (m, 2H), 7.82-7.59 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-4b1a08e6ff9240a2bb9541e3e60418c8
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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