4-Benzyloxyaniline → (4-(Benzyloxy)phenyl)hydrazine monohydrochloride

HRID 351220Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]([O-])=O.[Na+].[Sn](Cl)(Cl)(Cl)[Cl:21]>Cl.O>[ClH:21].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][NH2:16])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 3 °C

Procedure

To the suspension of 4-benzyloxyaniline (10 g) in concentrated hydrogen chloride (100 ml) was added dropwise a solution of sodium nitrite (3.2 g) in water (10 ml) over 10min at between −15 and −10° C., and then the mixture was stirred at 3° C. for 1 hr. To the mixture was added dropwise a solution of tin chloride (33.5 g) in concentrated hydrogen chloride (80 ml) at between −20 and −10° C. over 30 min, and then the mixture stirred at 0° C. for 1 hr.

Workup

stirringthe mixture stirred at 0° C. for 1 hr

Sources & evidence

ORD record: ord-0cfe48beef194a969cfbe38f55b4a80b
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183306B2

Reaction notes

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