HCID 24959803, compound → HCID 24959804, compound

HRID 1925095Notes

Reaction equation

HRID 1925095 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[C:12]3[CH:14]=[CH:15][C:16]([N+:18]([O-])=O)=[CH:17][C:11]=3[CH2:10][O:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:21][CH3:22])[C:4]=1[O:23][CH3:24]>C(OCC)(=O)C.[Pd]>[CH3:22][O:21][C:5]1[C:4]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[C:13]2[C:12]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:11]=3[CH2:10][O:9][CH2:8][C:7]=2[CH:6]=1

Participants

4

Reactant 1

HCID 24959803HCID 24959803, compound

Product 1

HCID 24959804HCID 24959804, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,2,3-Trimethoxy-9-nitro-5,7-dihydrodibenzo[c,e]oxepine (Example 5, 85.4 mg, 0.258 mmol) in ethyl acetate (4 mL) containing palladium on charcoal (10% w/w; 7 mg) was stirred under a hydrogen balloon for 24 hours until TLC indicated the consumption of starting material. The mixture was passed through a plug of neutral alumina (0.5 cm depth in a Pasteur pipette) and concentrated in vacuo to afford the title compound as a yellow crystalline solid (70 mg, 91%); m.p. 145° C.; High Resolution Mass Spectrometry Found: M 301.1305 (C17H19NO4 requires 301.1314); νmax/cm−1 (thin film) 3461, 3361, 2938, 2852, 1607, 1482; NMR Spectrum δH (400 MHz, CDCl3) 3.66 (3H, s, OCH3), 3.78 (2H, br s, NH2), 3.91 (3H, s, OCH3), 3.94 (3H, s, OCH3), 4.03-4.18 (2H, br m, 5-H or 7-H), 4.30-4.44 (2H, br m, 5-H or 7-H), 6.74 (1H, s, 8-H), 6.745 (1H, d, J 2.5 Hz, 4-H), 6.77 (1H, dd, J 2.5, 8.2 Hz, 2-H), 7.52 (1H, d, J 8.2 Hz, 1-H); NMR Spectrum δC (100 MHz, CDCl3) 56.44, 61.12, 61.50, 68.11, 68.15, 109.08, 115.26, 116.12, 127.20, 127.47, 130.97, 131.34, 136.64, 143.09, 150.92, 152.79; m/z (ES) 301 (M, 20%); Rf (petroleum ether 60-80°—ethyl acetate 2:3) 0.32.

Workup

  1. customthe consumption of starting material
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55ace5c7a68d4a218969a0beed89b0fb
Source dataset
uspto-grants-2012_05
Patent number
US08178578B2

Reaction notes

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