HCID 10686022, compound → HCID 135471320, compound

HRID 356984Notes

Reaction equation

HRID 356984 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:19](=[NH:23])[O:20][CH2:21][CH3:22])C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:19](=[NH:23])[O:20][CH2:21][CH3:22]

Participants

4

Reactant 1

HCID 10686022HCID 10686022, compound

Product 1

HCID 135471320HCID 135471320, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 2.57 g) was introduced into a solution of 13 (15.21 g, 49.8 mmol) in ethanol (430 ml). The suspension was stirred under a hydrogen atmosphere for 6 hours. After filtration through Celite, the filtrate was concentrated, giving 10.11 g (94%) of 14 as yellow crystals, mp 145°-146° C. IR (KBr): 2980 (C--H), 1620 (C=C), 1085 (C--O) cm-1. 1H NMR: δ8.65 (d, 1 arom H), 7.76 (d, 1 arom H), 7.71 (d, 1 arom H), 7.47 (m, 1 arom H), 7.29 (m, 1 arom H), 7.15 (d, 1 arom H), 4.29 (q, 1 CH2, J=7 Hz), 1.42 (t, 1 CH3). Anal. (C13H13NO2) C, H, N.

Workup

  1. filtrationAfter filtration through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b0311cb63aa747d7a526bdb1b063c841
Source dataset
uspto-grants-1998_11
Patent number
US05840739

Reaction notes

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