HCID 67271937, compound → HCID 67271920, compound

HRID 1696489Notes

Reaction equation

HRID 1696489 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N+:16]([O-])=O)[CH:7]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([NH2:16])[CH:7]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67271937HCID 67271937, compound

Product 1

HCID 67271920HCID 67271920, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (3-nitronaphthalen-1-yl)-acetic acid ethyl ester (3 g, 11.58 mmol) and 10% Pd/C (300 mg) in EtOH (100 mL) was stirred under H2 atmosphere (45 psi) at RT overnight. The mixture was filtered over Celite® and washed with EtOH. The filtrate was concentrated to afford (3-aminonaphthalen-1-yl)-acetic acid ethyl ester, which was put to the next reaction without further purification. 1H NMR (300 MHz, DMSO-d6), δ 7.65 (d, J=8.1 Hz, 1H), 7.48 (d, J=8.1 Hz, 1H), 7.27 (t, J=8.1 Hz, 1H), 7.08 (t, J=8.1 Hz, 1H), 6.85 (s, 1H), 6.73 (s, 1H), 5.35 (s, 2H), 4.06 (d, J=7.2 Hz, 2H), 3.94 (s, 2H), 1.14 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 260 (M+H+).

Workup

  1. filtrationThe mixture was filtered over Celite®
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dead3fa8565044cc94a26309aa2f10b0
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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