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

HRID 989370Notes

Reaction equation

HRID 989370 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 catalyst is filtered through a pad of Celite, 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 washed with methylene chloride and ethyl acetate. The filtrate is evaporated to yield 3.4 g of 3-amino-6-hydroxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester as a yellow solid, mp 262-263° C.

Workup

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

Sources & evidence

ORD record
ord-8cc5bb697ec042148cde66138a42bb1a
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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