Stannous Chloride → (4-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)phenyl)hydrazine Hydrochloride

HRID 2040593Notes

Reaction equation

Cl.[CH:2]1([C:7]2[CH:21]=[CH:20][C:10]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=3)=[CH:9][C:8]=2[C:22]([F:25])([F:24])[F:23])[CH2:6][CH2:5][CH2:4][CH2:3]1.[N:26]([O-])=O.[Na+].[Sn](Cl)[Cl:31]>O.Cl>[ClH:31].[CH:2]1([C:7]2[CH:21]=[CH:20][C:10]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([NH:17][NH2:26])=[CH:18][CH:19]=3)=[CH:9][C:8]=2[C:22]([F:23])([F:24])[F:25])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -1 °C

Procedure

4-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)aniline hydrochloride (30 g, 81 mmol) was suspended in water (285 mL), and concentrated HCl (18 mL) was added. The suspension was stirred efficiently and cooled in ice/IPA bath to −0° C. Sodium nitrite (5.57 g, 81 mmol) in water (12 mL) was added. After addition, the reaction was stirred at 2° C. for 40 minutes. Some solids on the side were washed with ACN (10 mL). The mixture was cooled to −1° C. and tin (II)chloride (45.9 g, 242 mmol) dissolved in concentrated HCl (30 mL) was added slowly. A thick precipitate was formed and stirring was continued for 30 minutes. The mixture was warmed to room temperature and stirred for 3 h. The mixture was filtered, washed with HCl (0.1 M) and the solid was dried under vacuum to give the title compound (40.6 g).

Workup

additionAfter addition
stirringthe reaction was stirred at 2° C. for 40 minutes
washSome solids on the side were washed with ACN (10 mL)
additionwas added slowly
customA thick precipitate was formed
stirringstirring
temperatureThe mixture was warmed to room temperature
stirringstirred for 3 h
filtrationThe mixture was filtered
washwashed with HCl (0.1 M)
customthe solid was dried under vacuum

Sources & evidence

ORD record: ord-f68fffd89f4c4b17876632ee9a91a9ec
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580841B2

Reaction notes

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