Hydrochloric Acid → Methyl 2-[(5-amino-6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate, hydrochloride salt

HRID 259673Notes

Reaction equation

HRID 259673 reaction equation
[Cl:1][C:2]1[C:17]([N+:18]([O-])=O)=[CH:16][C:5]2[C:6]([O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[N:7][O:8][C:4]=2[CH:3]=1.Cl.[H][H]>[Pd].C(O)C>[ClH:1].[NH2:18][C:17]1[C:2]([Cl:1])=[CH:3][C:4]2[O:8][N:7]=[C:6]([O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22402917Methyl 2-[(6-chloro-5-nitro-1,2-benzisoxazol-3-yl)oxy]propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 131719244Methyl 2-[(5-amino-6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate, hydrochloride salt

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of methyl 2-[(6-chloro-5-nitro-1,2-benzisoxazol-3-yl)oxy]propionate (2.0 g, 6.7 mmol), 5% palladium on activated carbon (0.1 g) and concentrated hydrochloric acid (0.6 mL) in ethanol is hydrogenated until 430 mL of hydrogen is taken up. The reaction mixture is then filtered through diatomaceous earth and concentrated in vacuo to give the title product as a brown gum which is identified by NMR spectral analyses.

Workup

  1. filtrationThe reaction mixture is then filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bac2ae8559334b3fae50a5827a73f645
Source dataset
uspto-grants-1996_06
Patent number
US05523278

Reaction notes

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