Acetic Acid → HCID 131724306, compound

HRID 1840403Notes

Reaction equation

HRID 1840403 reaction equation
C(O[C:4]([CH:6]1[C:14](=[O:15])[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]1=[O:16])=[O:5])C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:25][C:4]([CH:6]2[C:14](=[O:15])[C:13]3[N:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]2=[O:16])=[O:5])[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 108243-MethoxyanilineHCID 12646941HCID 12646941, compound

Product 1

HCID 131724306HCID 131724306, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,7-Dioxo-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid ethyl ester (100 mg) (see D. Binder, Monatshefte für Chemie, Vol. 105, Pp. 179-186, 1974), m-anisidine (0.124 ml) and acetic acid (0.052 ml) were suspended in toluene (5 ml). This mixture was refluxed for 2 hours under nitrogen. The mixture was cooled to room temperature and the ppt was collected with suction. The ppt was washed with toluene and dichloromethane and dried under reduced pressure to give a brown powder (112 mg). ESI−MS: m/z 297 (MH+); 1H-NMR (DMSO-d6): δ3.74 (3H, s), 6.54 (1H, dd, J=8.5 Hz, J=2.5 Hz), 7.04 (1H, bd, J=8.5 Hz), 7.16 (1H, t, J=8.5 Hz), 7.38 (1H, dd, J=7.0 Hz, 4.5 Hz), 7.44 (1H, t-like, 2.5 Hz), 7.70 (1H, dd, J=7.0 Hz, 1.5 Hz), 8.57 (1H, dd, J=4.5 Hz, 1.5 Hz), 10.79 (1H, s).

Workup

  1. temperatureThis mixture was refluxed for 2 hours under nitrogen
  2. customthe ppt was collected with suction
  3. washThe ppt was washed with toluene and dichloromethane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-615281d31cca4afb8913cdeecaa60f9a
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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