Hydrochloric Acid → N-(5-Methylisoxaz-3-oyl)-3-Aminobenzylamine

HRID 840585Notes

Reaction equation

HRID 840585 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)=[O:8])[CH:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)=[O:8])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 47450419N-(5-Methylisoxaz-3-oyl)-3-NitrobenzylamineHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 66156126N-(5-Methylisoxaz-3-oyl)-3-AminobenzylamineYield 86.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 260 mg (1.00 mmol) of N-(5-methylisoxaz-3-oyl)-3-nitrobenzylamine in 20 mL of tetrahydrofuran was added 674 mg (3.00 mmol) of tin chloride dihydrate, followed by 2 ml of concentrated hydrochloric acid. The reaction was stirred at room temperature for 18 hours and then diluted with 100 mL of ethyl acetate. The organic solution was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated to give 200 mg (86%) of the title compound as a yellow foam. MS(FD) m/z 231 (M+).

Workup

  1. washThe organic solution was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4209da9266e549af8655969e26880e61
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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