Succinic anhydride → 5-Succinimido-2-(2-phenylchroman-6-yloxy)-pyridine

HRID 31237Notes

Reaction equation

HRID 31237 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[O:15][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]3)=[N:6][CH:7]=1.[C:25]1(=O)[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>C(O)(=O)C>[C:25]1(=[O:30])[N:1]([C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[O:15][CH:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:13][CH2:12]4)=[N:6][CH:7]=2)[C:28](=[O:29])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridine

Product 1

HCID 179784915-Succinimido-2-(2-phenylchroman-6-yloxy)-pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-2-(2-phenylchroman-6-yloxy)-pyridine of Example 26 (0.16 g) was dissolved in 7.5 ml of glacial acetic acid under nitrogen. Succinic anhydride (0.0563 g) was added and the solution refluxed 60 minutes and solution was cooled and evaporated to dryness. Toluene (25 ml) was added and evaporated again to dryness. Product was purified by column chromatography (CH2Cl2:i-PrOH /95:5 as the eluant. 1H-NMR (400 MHz; d6-DMSO): δ 8.03 (d, 1H, J=2.6 Hz), 7.73 (dd, 1H, J=8.7 Hz, J=2.6 Hz), 7.48-7.31 (m, 5H), 7.10 (d, 1H, J=8.7 Hz), 6.95 (d, 1H, J=2.6 Hz), 6.92 (dd, 1H, J=8.7 Hz, J=2.7 Hz), 6.88 (d, 1H, J=8.6 Hz), 5.13 (dd, 1H, J=10.2 Hz, J=2.2 Hz), 3.05-2.92 (m, 1H), 2.84-6.68 (m, 1H), 2.79 (s, 4H), 2.22-2.12 (m, 1H), 2.08-1.93 (m, 1H).

Workup

  1. temperaturethe solution refluxed 60 minutes
  2. temperaturesolution was cooled
  3. customevaporated to dryness
  4. additionToluene (25 ml) was added
  5. customevaporated again to dryness
  6. customProduct was purified by column chromatography (CH2Cl2

Sources & evidence

ORD record
ord-b83cdd95e34b487c9947965d11db7794
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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