HCID 67520240, compound → HCID 67520047, compound

HRID 1925307Notes

Reaction equation

HRID 1925307 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[C:12]2[N:23](CC1C=CC=CC=1)CC1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd]>[CH3:22][O:21][C:19]([C:15]1[C:16]2[C:11](=[CH:10][C:9]([OH:8])=[CH:18][CH:17]=2)[C:12]([NH2:23])=[CH:13][CH:14]=1)=[O:20]

Participants

4

Reactant 1

HCID 67520240HCID 67520240, compound

Product 1

HCID 67520047HCID 67520047, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd on carbon (5 wt %, 0.350 g) was added to a solution of methyl 6-(benzyloxy)-4-(dibenzylamino)-1-naphthoate (3.409 g, 6.834 mmol) in MeOH (70 mL). The system was evacuated and purged with argon and then stirred under a H2 (g) atmosphere for 20 h. The mixture was filtered through a pad of Celite and concentrated to afford methyl-4-amino-6-hydroxy-1-naphthoate as a light brown solid. MS (ESI, pos. ion) m/z: 218.1 (M+H). Mass Calc'd for C12H11NO3: 217.

Workup

  1. customThe system was evacuated
  2. custompurged with argon
  3. filtrationThe mixture was filtered through a pad of Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-956131c0fc96432d9e37c5b2a80db6bb
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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