Acetic Anhydride → N-Acetyl-2-(2-Penylchroman-6-yloxy)-aniline

HRID 31233Notes

Reaction equation

HRID 31233 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[NH2:20])[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:25]([NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:16][CH2:15]2)(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 179785582-(2-Phenylchroman-6-yloxy)-aniline

Product 1

HCID 131727057N-Acetyl-2-(2-Penylchroman-6-yloxy)-aniline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

2-(2-Penylchroman-6-yloxy)-aniline (0.093 g) was dissolved in 1 ml of dry pyridine under nitrogen. DMAP (10 mol-%) and acetic acid anhydride (0.1 ml) were added and the solution was stirred for 4 hours at room temperature followed with quenching with 0.5 ml of H2O. The solution was evaporated to dryness and toluene was added and evaporated again. Toluene evaporation was repeated. Product was purified by column chromatography (CH2Cl2:i-PrOH/98:2 as the eluant) and recrystallized from 0.5 ml of heated absolute ethanol by cooling and adding 0.5 ml of 1H-NMR (400 MHz; d6-DMSO): δ 9.43 (s, 1H), 7.96 (m, 1H), 7.48-7.30 (m, 5H), 7.08-6.99 (m, 2H), 6.89-6.74 (m, 4H), 5.10 (dd, 1H, J=9.9, J=2.0), 3.03-2.88 (m, 1H), 2.76-2.65 (m, 1H), 2.21-2.11 (m, 1H), 2.10-1.91 (m, 1H), 2.06 (s, 3H).

Workup

  1. customwith quenching with 0.5 ml of H2O
  2. customThe solution was evaporated to dryness and toluene
  3. additionwas added
  4. customevaporated again
  5. customToluene evaporation
  6. customProduct was purified by column chromatography (CH2Cl2
  7. customi-PrOH/98:2 as the eluant) and recrystallized from 0.5 ml of heated absolute ethanol
  8. temperatureby cooling
  9. additionadding 0.5 ml of 1H-NMR (400 MHz; d6-DMSO): δ 9.43 (s, 1H), 7.96 (m, 1H), 7.48-7.30 (m, 5H), 7.08-6.99 (m, 2H), 6.89-6.74 (m, 4H), 5.10 (dd, 1H, J=9.9, J=2.0), 3.03-2.88 (m, 1H), 2.76-2.65 (m, 1H), 2.21-2.11 (m, 1H), 2.10-1.91 (m, 1H), 2.06 (s, 3H)

Sources & evidence

ORD record
ord-7b8694635ceb4bd79790599b44b0d5a4
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…