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

HRID 375067Notes

Reaction equation

HRID 375067 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-70bd94d66a5c49eb8cc82faabcea7b22
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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