HCID 10156578, compound → 3-Amino-6-hydroxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester

HRID 902411Notes

Reaction equation

HRID 902411 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:17]([NH2:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:19]CC3C=CC=CC=3)[CH:14]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.CO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([C:8]1[C:17]([NH2:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([OH:19])[CH:14]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 1

HCID 10156578HCID 10156578, compound

Product 1

HCID 120627383-Amino-6-hydroxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl esterYield 97.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.7 g (12.0 mmol) of 3-amino-6-benzyloxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester and 2.0 g of 10% Pd/C in 40 mL of DMF and 100 mL of methanol is shaken on Parr shaker at 40 psi for 18 hours. The hydrogenation is repeated twice more to bring the reaction to completion. The catalyst is filtered through a pad of Celite, is washed with methanol and solvent is evaporated to yield a residue which is dissolved in methylene chloride. This is then filtered through a short pad of Magnesol and is washed with methylene chloride and ethyl acetate. The filtrate is evaporated to yield 3.4 g of 3-amino-6-hydroxy-7-methoxy-naphthalene-2-carboxylic acid tert-butyl ester as a yellow solid, mp 262-263° C.

Workup

  1. customthe reaction to completion
  2. filtrationThe catalyst is filtered through a pad of Celite
  3. washis washed with methanol and solvent
  4. customis evaporated
  5. customto yield a residue which
  6. filtrationThis is then filtered through a short pad of Magnesol
  7. washis washed with methylene chloride and ethyl acetate
  8. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-3d4c7bc2450f49c294da761856928438
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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