Methanol → HCID 67598756, compound

HRID 1490288Notes

Reaction equation

HRID 1490288 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=O)[C:5]1=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](OC)[C:16]=1[N+:23]([O-])=O)(=[O:3])[CH3:2].[CH3:26][OH:27]>[Pd]>[CH3:26][O:27][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:6]1[N:23]=[C:16]3[C:15](=[CH:14][C:5]=1[N:4]2[C:1](=[O:3])[CH3:2])[CH:20]=[CH:19][CH:18]=[CH:17]3

Participants

4

Reactant 2

HCID 887MethanolHCID 53829696HCID 53829696, compound

Product 1

HCID 67598756HCID 67598756, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

A suspension of 1-acetyl-2-(3-methoxy-2-nitrophenylmethylene)-3-oxo-2,3-dihydroindole from Example 35 (460 mg, 1.36 mmol), 10% Pd/C (70 mg) and MeOH (17 mL) was stirred under H2 at atmospheric pressure (balloon) for 3 hours. Additional Pd/C (70 mg) was added, a fresh balloon of H2 was attached and the mixture was stirred at room temperature overnight. The Pd/C catalyst was filtered over celite and the filtrate was evaporated. The resulting crude yellow product (209 mg, >100%) was purified by LPLC, eluting with CH2Cl2, then CH2Cl2 /EtOAc (3:97), to obtain 208 mg (53%) of the title compound as a colorless solid, Rf 0.47 (hexane-EtOAc 1:1), mp 125.1°-125.8° C.; 1H NMR (CDCl3) δ 9.02 (s, 1H), 8.62 (dd, J=7.6; J=0.8 1H), 8.13 (d, J=8.4, 1H), 7.65 (dt, J=8.0; J=0.8, 1H), 7.59 (d, J=8.4, 1H), 7.53 (m, 2H), 7.11 (d, J=7.6, 1H), 4.18 (s, 3H), 2.97 (s, 3H); 13C NMR (CDCl3) δ 169.8, 155.2, 146.5, 141.4, 138.1, 131.9, 130.5, 128.6, 126.3, 124.3, 124.2, 122.7, 121.6, 120.5, 115.6, 106.7, 56.2, 27.7; MS (EI, m/z) 290 (M+).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationThe Pd/C catalyst was filtered over celite
  3. customthe filtrate was evaporated
  4. customThe resulting crude yellow product (209 mg, >100%) was purified by LPLC
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-75587fb957004de899a5fccb0aa9ebe2
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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