Acetic Anhydride → HCID 11849245, compound

HRID 422118Notes

Reaction equation

HRID 422118 reaction equation
O[NH:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[NH:25])[NH:23]O)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=[NH:4].[C:26]([O:29]C(=O)C)(=[O:28])[CH3:27]>C(O)(=O)C.[Pd]>[C:26]([OH:29])(=[O:28])[CH3:27].[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:7]3[O:6][C:5]([C:3]([NH2:4])=[NH:2])=[CH:9][CH:8]=3)=[CH:11][CH:12]=2)=[CH:21][CH:20]=1)(=[NH:23])[NH2:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178513261HCID 178513261, compound

Product 1

HCID 11849245HCID 11849245, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3 (1 mmol) in glacial acetic acid (10 mL) was slowly added acetic anhydride (0.35 mL). After stirring for overnight TLC indicated complete acylation of the starting material, then was added 10% palladium on carbon (80 mg). The mixture was placed on Parr hydrogenation apparatus at 50 psi for 4 h at room temperature. The mixture was filtered through hyflo and the filter pad washed with water. The filtrate was evaporated under reduced pressure and the precipitate was collected and washed with etherto give 5 in 71% yield, mp 236-238° C. 1H NMR (D2O/DMSO-d6); δ 1.78 (s, 2×CH3), 7.31 (d, J=3.6 Hz, 1H), 7.61 (d, J=3.6 Hz, 1H), 7.85-8.11 (m, 8H). EIMS m/e (rel. int.); 304 (M+, 20), 287 (100), 270 (50), 216 (30), 190 (10). High resolution Calc. for C18H16N4O ms 304. 13241. Observed 5 304. 13201. Anal. Calc. for C16H14N4O2-2.0AcOH-1.75H2O-0.25EtOH: C %, 57.81; H %, 6.25; N %, 11.98. Found C %, 58.18; H %, 5.90; N %, 11.56.

Workup

  1. waitThe mixture was placed on Parr hydrogenation apparatus at 50 psi for 4 h at room temperature
  2. filtrationThe mixture was filtered through hyflo
  3. washthe filter pad washed with water
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe precipitate was collected
  6. washwashed with etherto
  7. customgive 5 in 71% yield, mp 236-238° C

Sources & evidence

ORD record
ord-0338fe8908894239a4443a2a71eaa33a
Source dataset
uspto-grants-2012_01
Patent number
US08101636B2

Reaction notes

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