Hydrochloric Acid → 4-(Pyrid-2-ylmethoxy)phenylhydrazine

HRID 1975738Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.Cl.[N:17]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>O.C(OCC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][NH2:17])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(Pyrid-2-ylmethoxy)aniline (86.7 g; 433 mmol), prepared as in step 2, was suspended in 200 mL water and 108 mL concentrated HCl was added. The solution was cooled to 0° C. and sodium nitrite (30.8 g; 446 mmol) in 75 mL water was added dropwise. The reaction was stirred for 1 hour at 0° C. The diazonium salt was then transferred dropwise to a solution of sodium hydrosulfite (85% purity; 487 g; 2.80 mol) in 2000 mL water, 2000 mL diethyl ether, and 20 mL 2N aqueous NaOH at 0°-5° C. with vigorous stirring. When addition was complete 775 mL 2N aqueous NaOH was added dropwise. The cooling bath was removed and the reaction was stirred at room temperature for 1 hour. The precipitate was collected by vacuum filtration and washed with water then diethyl ether. The reaction yielded 4-(pyrid-2-ylmethoxy)phenylhydrazine as a pale green solid.

Workup

additionWhen addition
additionwas added dropwise
customThe cooling bath was removed
stirringthe reaction was stirred at room temperature for 1 hour
filtrationThe precipitate was collected by vacuum filtration
washwashed with water

Sources & evidence

ORD record: ord-62fe497920174636ac6565bd8f3b595b
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288743

Reaction notes

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