Hydrochloric Acid → 3-{[3-(Diethylamino)propyl]amino}-1H-indazol-5-OL

HRID 484861Notes

Reaction equation

S(=O)(=O)(O)O.[CH2:6]([N:8]([CH2:22][CH3:23])[CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][N:14]=1)[CH3:7].[OH-:24].[K+].Cl>O>[CH2:22]([N:8]([CH2:6][CH3:7])[CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=2)[NH:15][N:14]=1)[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To 4.3 g of 95% sulfuric acid was added 9.25 g of the 3-(3-diethylaminopropylamino)indazole, and the mixture was stirred for 3 hours at 80° C. To the mixture was added 13 ml of water, and the pH of the mixture was adjusted to 14 with potassium hydroxide. The mixture was washed twice with 20 ml of chloroform, and water was removed under reduced pressure. To the residue thus obtained were added 12.5 g of potassium hydroxide and 0.6 ml of water, and the mixture was stirred for 8 hours at 250° C. After cooling, to the mixture was added hydrochloric acid to separate crystals. Then the crystals were obtained by filtration and dried to give 4.39 g of 3-(3-diethylaminopropylamino)-5-hydroxyindazole having the following analytical values in a yield of 40%.

Workup

washThe mixture was washed twice with 20 ml of chloroform, and water
customwas removed under reduced pressure
customTo the residue thus obtained
stirringthe mixture was stirred for 8 hours at 250° C
temperatureAfter cooling, to the mixture
customto separate crystals
customThen the crystals were obtained by filtration
customdried

Sources & evidence

ORD record: ord-7f23ee095c69474ea902030792f0dad3
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04533731

Reaction notes

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