Sodium Hydroxide → (3-Morpholin-4-yl-phenyl)-hydrazine

HRID 1784383Notes

Reaction equation

HRID 1784383 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N:14]([O-])=O.[Na+].O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl>[N:1]1([C:7]2[CH:8]=[C:9]([NH:13][NH2:14])[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 8477683-(Morpholin-4-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 55279390(3-Morpholin-4-yl-phenyl)-hydrazineYield 79%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a cooled (−5 ° C.) solution of 3-morpholin-4-yl-phenylamine (44)(0.18 g, 1.00 mmol) in 2M HCl(aq) was added sodium nitrite (69 mg, 1.00 mmol in 1 ml water) dropwise. The red solution was stirred at −5° C. for 10 minutes before the addition of tin (II) chloride dihydrate (1.13 g, 5.0 mmol). The mixture was stirred vigorously and allowed to warm to room temperature over the period of 1 hour. 2M NaOH(aq) was added until the solution was basic (pH=8), then extracted with EtOAc (2×20 ml). The combined organic extracts were dried using MgSO4, filtered and concentrated in vacuo to give the desired product (0.15 g, 79.0%) (3-Morpholin-4-yl-phenyl)-hydrazine. m/z (LC-MS, ESP): 194.4 [M+H]+, R/T=1.00 mins.

Workup

  1. extractionextracted with EtOAc (2×20 ml)
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c99b7303929b490fb4c110647f7dc8c3
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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