Hydrazine hydrate (1:1) → HCID 136359760, compound

HRID 1754551Notes

Reaction equation

HRID 1754551 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([CH:13]=O)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.O.[NH2:17][NH2:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[NH:18][N:17]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86679789HCID 86679789, compound

Product 1

HCID 136359760HCID 136359760, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-bromo-4-chloro-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (8.0 g, 27.9 mmol) in 150 mL of DMF at 80° C. is added hydrazine hydrate (2 mL, 33.5 mmol) at 80° C. The reaction medium is stirred for 24 hours at 80° C. and then cooled to room temperature and filtered. The solid obtained is washed with diisopropyl ether and dried to give 5.3 g of 7-bromo-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one in the form of a pale yellow powder (yield: 72%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe solid obtained
  4. washis washed with diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-b58c7ed2093a4b8e9a2cb014cc726dc1
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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