Isopropanol → 5-Chloro-2-(3-methylisoxazol-5-ylmethoxy)benzylamine

HRID 392906Notes

Reaction equation

HRID 392906 reaction equation
CC(O)C.O.NN.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:27][CH2:28][C:29]2[O:33][N:32]=[C:31]([CH3:34])[CH:30]=2)=[C:13]([CH:26]=1)[CH2:14][N:15]1C(=O)C2C(=CC=CC=2)C1=O>C1COCC1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:27][CH2:28][C:29]2[O:33][N:32]=[C:31]([CH3:34])[CH:30]=2)=[C:13]([CH:26]=1)[CH2:14][NH2:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24654Hydrazine hydrate (1:1)HCID 226617672-[5-Chloro-2-(3-methylisoxazol-5-ylmethoxy)benzyl]isoindole-1,3-dione

Product 1

HCID 226618715-Chloro-2-(3-methylisoxazol-5-ylmethoxy)benzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a flask containing anhydrous 2-propanol (40 mL), hydrazine hydrate (4 mL, and anhydrous THF (60 mL), at room temperature, was added 2-{5-chloro-2-(3-methylisoxazol-5-ylmethoxy)benzyl]isoindole-1,3-dione (5 g, 13 mmol). The reaction was stirred at 50° C. for 3 h. The solids were filtered and washed with THF. The filtrate was concentrated, dissolved in ether (100 ml) and washed with 1N NaOH (1×) and brine, dried (MgSO4), filtered and concentrated to afford the title product as a solid.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in ether (100 ml)
  5. washwashed with 1N NaOH (1×) and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c1602f721ac4206903a355811952356
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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