3-hydroxy-4-nitro-3H-isobenzofuran-1-one → 4-Amino-3-hydroxyphthalide

HRID 326809Notes

Reaction equation

HRID 326809 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-])=O)[C:4](=[O:5])[O:3]1>O1CCCC1.[Pd]>[NH2:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:2]([OH:1])[O:3][C:4]2=[O:5]

Participants

4

Reactant 1

HCID 110955283-hydroxy-4-nitro-3H-isobenzofuran-1-one

Product 1

HCID 151807284-Amino-3-hydroxyphthalide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10 g of 3-hydroxy-4-nitro-phthalide are dissolved in 100 ml of tetrahydrofuran and, after addition of 1 g of palladium on barium sulphate (5%), the mixture is hydrogenated at atmospheric pressure and 20°-25° C. The catalyst is filtered off and the filtrate is concentrated. The evaporation residue is stirred with ether and filtered off with suction. 5.8 g (68.5% of theory) of a colourless substance of melting point 280°-285° C. (dec.) are obtained.

Workup

  1. customis hydrogenated at atmospheric pressure and 20°-25° C
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated
  4. filtrationfiltered off with suction
  5. custom5.8 g (68.5% of theory) of a colourless substance of melting point 280°-285° C. (dec.) are obtained

Sources & evidence

ORD record
ord-cf5750770f3449e0a1550b7a704f6820
Source dataset
uspto-grants-1993_12
Patent number
US05270469

Reaction notes

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