Methyl 4-hydrazinobenzoate hydrochloride → HCID 178498108, compound

HRID 2243412Notes

Reaction equation

HRID 2243412 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)C.Cl.[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([NH:36][NH2:37])=[CH:32][CH:31]=1>C(O)CCC.C(OC)(C)(C)C>[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:31]=[CH:32][C:33]([N:36]2[C:4](=[O:3])[C:6]3=[C:7]([C:17]4[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=4)[NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:15]3=[N:37]2)=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 2788448Methyl 4-hydrazinobenzoate hydrochlorideHCID 58601129HCID 58601129, compound

Product 1

HCID 178498108HCID 178498108, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-Chloro-2-(4-nitrophenyl)-quinoline-3-carboxylic acid ethyl ester (2.86 g, 0.008 mol) and 4-hydrazino-benzoic acid methyl ester hydrochloride (1.7 g, 0.008 mol) were stirred in n-butanol (70 mL) at 120° C. for 24 h. The bright orange suspension was diluted with tert-butylmethyl ether, filtered, washed with cold heptane and left to dry under suction to yield 4-[4-(4-nitrophenyl)-3-oxo-3,5-dihydropyrazolo[4,3-c]quinolin-2-yl]-benzoic acid methyl ester (2.7 g, 76%) as an orange solid, LCMS m/z 441.35 [M+H]+ @ RT 1.66 min: 84% purity.

Workup

  1. filtrationfiltered
  2. washwashed with cold heptane
  3. waitleft
  4. customto dry under suction

Sources & evidence

ORD record
ord-84cac131152645f3990b7bbb8b7ed1c8
Source dataset
uspto-grants-2010_03
Patent number
US07674906B2

Reaction notes

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