(3-chloro-4-methoxyphenyl)hydrazine → HCID 178492081, compound

HRID 323636Notes

Reaction equation

HRID 323636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][NH2:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:12]([C:16]1[C:17]([C:28](Cl)=[O:29])=[N:18][C:19]2[C:24]([C:25]=1[OH:26])=[CH:23][CH:22]=[C:21]([Cl:27])[CH:20]=2)(OC)=[O:13]>O1CCCC1.O.Cl>[Cl:27][C:21]1[CH:22]=[CH:23][C:24]2[C:25](=[O:26])[C:16]3[C:12]([OH:13])=[N:11][N:10]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=4)[C:28](=[O:29])[C:17]=3[NH:18][C:19]=2[CH:20]=1

Participants

6

Reactant 2

HCID 5152072(3-chloro-4-methoxyphenyl)hydrazineHCID 178498566HCID 178498566, compound

Product 1

HCID 178492081HCID 178492081, compoundYield 48.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-chloro-4-methoxyphenylhydrazine (4.26 g, 24.7 mM) in 35b.) in tetrahydrofuran (200 mL) was added a solution of 3-carbomethoxy-7-chloro-4-hydroxyquinoline-2-carbonyl chloride (3.54 g, 11.8 mM, as prepared in Example 35b.) in tetrahydrofuran (100 mL) at 0° C. The resulting yellow suspension was stirred at 0° C. for 30 minutes and diluted with water (200 mL) to give a yellow solution. This solution was further diluted with hydrochloric acid (600 mL, 1N) to give a tan suspension which was stirred for 1 hour. The suspension was filtered (the filtrate was saved) and the collected solids were washed with water and then ether to give the title compound (2.30 g, 45%) as a tan powder, MS(CI): 436 (M+H), which was used above in the synthesis described for 7-chloro-3-(3-chloro-4-methoxyphenyl)-1-hydroxy-3,4,5,10-tetrahydropyridazino[4,5-b]quinoline-4,10-dione. 1H NMR 12.69 (s, 1H, exchangeable), 10.72 (s, 1H, exchangeable), 8.14 (d, J=8.50 Hz, 1H), 8.00 (br s, 1H, exchangeable), 7.76 (s, 1H), 7.48 (d, J=8.50 Hz, 1H), 7.05 (d, J=8.80 Hz, 1H), 6.98 (d, J=2.28 Hz, 1H), 6.85 (dd, J=2.28, 8.80 Hz, 1H), 3.78 (s, 3H), 3.70 (s, 3H). After sitting for five days, further precipitation occurred in the above saved acidic filtrate. The solids were collected to provide material (1.80 g) consisting of a mixture of the title compound (60%), 7-chloro-2-(3-chloro-4-methoxyphenyl)-1-hydroxy-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (35%) and 7-chloro-3-(3-chloro-4-methoxyphenyl)-1-hydroxy-3,4,5,10-tetrahydropyridazino[4,5-b]quinoline-4,10-dione (5%).

Workup

  1. customto give a yellow solution
  2. customto give a tan suspension which
  3. stirringwas stirred for 1 hour
  4. filtrationThe suspension was filtered (the filtrate
  5. washwere washed with water

Sources & evidence

ORD record
ord-3dab552ffb7a4a6da6298913996bb26b
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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