1-Methyl-1H-pyrrole-2-carbaldehyde → HCID 178496310, compound

HRID 845581Notes

Reaction equation

HRID 845581 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][OH:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9].[CH3:30][N:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.ClCCl>[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21](=[CH:36][C:32]3[N:31]([CH3:30])[CH:35]=[CH:34][CH:33]=3)=[O:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9]

Participants

7

Reactant 3

HCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 24436Sodium SulfateHCID 14183058HCID 14183058, compound

Product 1

HCID 178496310HCID 178496310, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of hydroxyamine 55 (0.80 g, 2 mmol) in anhydrous ethyl alcohol (5 mL) and toluene (20 mL) was added 1-methyl-2-pyrrolecarboxaldehyde (66) (0.22 g, 2 mmol) and Na2SO4 (0.30 g). The resulting mixture was heated at reflux for 48 h. The mixture was diluted with dichloromethane (100 mL) and dried (MgSO4), and the solvent was removed with a rotary evaporator. The crude product was purified by flash chromatography with 9:1 ethyl acetate/methanol as the eluant to obtain 0.40 g (0.8 mmol, 40%) of 77 as a light yellow solid: mp 173°-175° C.; IR (CH2Cl2) 3440, 2940, 1695, 1622, 1575, 1470, 1300, 1212, 1100 cm-1 ; 1H NMR (CDCl3) δ 1.10 (d, J=6.2 Hz, 3H), 1.22 (d, J=6.2 Hz, 3H), 2.26 (s, 6H), 3.31 (s, 3H), 3.55 (t, J=4.8 Hz, 2H), 3.71 (s, 3H), 4.11-4.20 (m, 2H), 4.94 (septet, J=6.2 Hz, 1H), 5.08 (s, 1H), 6.30-7.98 (m, 9H); 13C NMR (CDCl3) δ 19.17, 19.32, 22.01, 22.23, 34.34, 39.98, 58.79, 62.76, 67.04, 70.71, 102.63, 103.45, 109.56, 117.39, 118.95, 121.24, 124.21, 125.59, 128.01, 128.23, 129.62, 145.20, 146.02, 148.30, 149.91, 167.12, 167.60; mass spectrum, m/e (relative intensity) 495 (M+, 3.1), 481 (15.5), 296 (100), 254 (86.1), 184 (90.2), 108 (48.3); high resolution mass spectrum, m/e 495.2362 (calcd. for C27H33N3O6, 495.2369).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 48 h
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed with a rotary evaporator
  5. customThe crude product was purified by flash chromatography with 9:1 ethyl acetate/methanol as the eluant

Sources & evidence

ORD record
ord-259c412c1eb940e19a9f1519b75d0933
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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