Pyridine → 3-chloro-N'-(3-nitrobenzoyl)benzohydrazide

HRID 76452Notes

Reaction equation

HRID 76452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].N1C=CC=CC=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])([O-:20])=[O:19]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH:8][C:24]([C:23]1[CH:27]=[CH:28][CH:29]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=1)=[O:25])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8495Benzoyl chloride, 3-nitro-HCID 742893-Chlorobenzohydrazide

Product 1

HCID 38545223-chloro-N'-(3-nitrobenzoyl)benzohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-chlorobenzohydrazide (1 equivalent) and pyridine (2 equivalents) in CH2Cl2 at 0° C. was added a CH2Cl2 solution of 3-nitrobenzoyl chloride (1 equivalents) and stirred at 0° C. for 1 h and then at room temperature for overnight. The resulting solution was concentrated and diluted with water, basified with NaHCO3, the solid was filtered, washed with water, dried and analyzed to obtain N′1-(3-chlorobenzoyl)-3-nitrobenzene-1-carbohydrazide. 1H NMR (DMSO-d6): δ 10.99 (s, 1H), 10.79 (s, 1H), 8.73 (bs, 1H), 8.43 (bdd, 1H, J=1.2 and 8.1 Hz), 8.33 (bdd, 1J, J=8.4 Hz), 7.95 (s, 1H), 7.87 (m, 2H), 7.67 (bdd, 1H, J=1.2 and 8.1 Hz), 7.57 (t, 1H, J=7.8 Hz); LCMS: purity: 85%; MS (m/e): 320 (MH+).

Workup

  1. waitat room temperature for overnight
  2. concentrationThe resulting solution was concentrated
  3. additiondiluted with water
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f1a78e7fefa343da993349dced0783bf
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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