HCID 10568525, compound → HCID 10490319, compound

HRID 2258558Notes

Reaction equation

HRID 2258558 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[C:4]([Cl:15])[C:3]=1[O:16]CC1C=CC=CC=1>CCO.[Pd]>[NH2:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[C:4]([Cl:15])[C:3]=1[OH:16]

Participants

4

Reactant 1

HCID 10568525HCID 10568525, compound

Product 1

HCID 10490319HCID 10490319, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Amino-6-benzyloxy-8-carboxy-5-chlorotetralin (33 mg, 0.10 mmol) was dissolved in EtOH (3 mL) and 5% Pd/C (4 mg) was added. Hydrogenation at room temperature and atmospheric pressure for 2 h, filtration, evaporation and vacuum-drying gave the title compound (21 mg). Mp: 147° C. (dec); 1H NMR (DMSO-d6): δ 7.9 (br, NH, OH), 2.66 (t, J=6.0 Hz, 2 H), 2.54 (t, J=6.7 Hz, 2 H), 1.70-1.64 (m, 2 H) , 1.63-1.57(m, 2 H) ; 13C NMR (DMSO-d6): δ 169.73, 138.12, 136.45, 128.13, 123.32, 121.36, 115.15, 27.86, 26.91, 22.45, 22.25; MS (EI, 70 eV): m/z (rel.int.) 243/241 (M+, 21/65), 225/223 (35/100), 197/195 (61/100).

Workup

  1. filtrationfiltration, evaporation
  2. customvacuum-drying

Sources & evidence

ORD record
ord-fb1b66d7d1c240c99dc96c9374758285
Source dataset
uspto-grants-1997_08
Patent number
US05661183

Reaction notes

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