Hydrazine hydrate (1:1) → 5,7-Dichloro-8-methoxyquinoline-3-carbohydrazide

HRID 1754103Notes

Reaction equation

HRID 1754103 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]([Cl:16])[CH:12]=[C:11]([Cl:17])[C:10]=2[O:18][CH3:19])=O)C.O.[NH2:21][NH2:22]>C(O)C>[Cl:16][C:13]1[CH:12]=[C:11]([Cl:17])[C:10]([O:18][CH3:19])=[C:9]2[C:14]=1[CH:15]=[C:6]([C:4]([NH:21][NH2:22])=[O:3])[CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57939343Ethyl 5,7-dichloro-8-methoxyquinoline-3-carboxylate

Product 1

HCID 579393445,7-Dichloro-8-methoxyquinoline-3-carbohydrazideYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5,7-dichloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester 27 (404 mg, 1.35 mmol) and hydrazine monohydrate (1.0 g) in ethanol (10 ml) was heated under reflux for 5 hours. Upon cooling, a white crystalline solid was deposited. This was isolated via filtration, washed with ethanol, and dried, yielding the hydrazide 28 (307 mg, 80%) as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ 10.32 (br, 1 H), 9.33 (d, J=2.4, 1 H), 8.89 (d, J=2.4, 1 H), 8.02 (s, 1 H), 4.66 (br, 2 H), 4.06 (s, 3 H).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureUpon cooling
  3. customThis was isolated via filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-1d8e7fa9e4af41969b3798c0e7557a1f
Source dataset
uspto-grants-2015_10
Patent number
US09169211B2

Reaction notes

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