Hydroxide → HCID 15678077, compound

HRID 260403Notes

Reaction equation

HRID 260403 reaction equation
C([O:4][CH:5]1[C:18]2[C:9](=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[C:15]([O:19][CH3:20])[CH:14]=[CH:13]3)[CH2:8][CH2:7][CH2:6]1)(=O)C.[OH-]>CO>[OH:4][CH:5]1[C:18]2[C:9](=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[C:15]([O:19][CH3:20])[CH:14]=[CH:13]3)[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 961HydroxideHCID 15678074HCID 15678074, compound

Product 1

HCID 15678077HCID 15678077, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Compound 281a (7.10 g, 26.2 mmol) in dry methanol (200 mL) was added Dowex 1×8-200 hydroxide form (1.00 g) and the resulting mixture was heated at 60° C. for 24 hours. The warm reaction mixture was filtered and the filtrate was distilled until 100 mL remained. Ethyl ether (100 mL) was added to the residue and the resulting solution was allowed to stand in the refrigerator at zero degrees C for 16 hours. The crystalline precipitate was filtered off, washed with ethyl ether (50 mL) to give 5.03 g (84 percent) of Compound 282a: white crystalline solid; mp 189.5°-190.5° C.; Rf =0.21 (silica, ethyl ether); IR (CHCl3) νmax 3156, 2931, 1621, 1508 cm-1 ; 1H NMR (300 Mz, CDCl3) δ 8.45 (s, 1 H, H6), 7.96 (d, J=9.2 Hz, 1 H, H4), 7.50 (d, J=2.6 Hz, 1 H, H3), 7.31 (dd, J=9.2, 2.6 Hz, 1 H, H1), 5.37 (br s, 1 H, H10), 3.97 (s, 3 H, OCH3), 2.97-2.75 (m, 2 H, H7), 2.75-2.30 (br s, 1 H, OH), 2.30 (br d, J=10.6 Hz, 1 H, H9), 2.07-1.96 (m, 3 H, H8 and H9); 13C NMR (125 Mz, DMSO-d6) δ 157.1, 149.7, 142.5, 140.2, 130.2, 129.7, 128.1, 119.7, 103.0, 61.0, 55.3, 31.8, 26.6, 16.7; MS (FAB+) m/e (rel intensity) 230 (M+H, 100), 212 (10);HRMS for C14H16NO2 (M+H), calcd 230.1181, found 230.1189. Anal. Calcd for C14H15NO2 : C, 73.34; H, 6.59; N, 6.11. Found: C, 73.16; H, 6.73; N, 6.08.

Workup

  1. customThe warm reaction mixture
  2. filtrationwas filtered
  3. distillationthe filtrate was distilled until 100 mL
  4. additionEthyl ether (100 mL) was added to the residue
  5. filtrationThe crystalline precipitate was filtered off
  6. washwashed with ethyl ether (50 mL)

Sources & evidence

ORD record
ord-2f63807a9bc74bb8ae34349db92c7298
Source dataset
uspto-grants-1996_06
Patent number
US05527805

Reaction notes

Loading…