Anthranilic Acid → HCID 66753771, compound

HRID 1182917Notes

Reaction equation

HRID 1182917 reaction equation
N1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]=2[N:4]=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])N=1.C(O)(=O)[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)N.C(ON=O)CC(C)C>O1CCOCC1.C(OCC)C>[CH2:7]1[C:6]2[C:5](=[N:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:17]3[C:18]=2[CH:20]=[CH:21][CH:22]=[CH:23]3)[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 227Anthranilic AcidHCID 8053Isoamyl NitriteHCID 66754398HCID 66754398, compound

Product 1

HCID 66753771HCID 66753771, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Analogously to the method described by Gonsalves et al. (Tetrahedron 1992, 48, 6821) a solution of 3.90 g of ethyl 5,6,7,8-tetrahydro-benzo[1,2,4]triazin-3-carboxylate (Sagi et al., Heterocycles 1989, 29, 2253) in 20 ml dioxane is refluxed. Then 8.22 g of anthranilic acid and 7.02 g of isoamylnitrite, in each case dissolved in 20 ml dioxane, are simultaneously added dropwise within 25 minutes by means of two dropping funnels. The reaction mixture is refluxed for a further 30 minutes. For working up the cooled deep-brown reaction solution is diluted with 150 ml diethyl ether, washed with 100 ml of 2 N sodium hydroxide solution and with water, dried over magnesium sulphate and evaporated down. The brown, oily flask residue is chromatographed through a silica gel column with ethyl acetate/petroleum ether (20:80 to 50:50) as eluant. The product obtained is still somewhat contaminated, but is reacted further without any more purification.

Workup

  1. temperatureis refluxed
  2. additionare simultaneously added dropwise within 25 minutes by means of two dropping funnels
  3. temperatureThe reaction mixture is refluxed for a further 30 minutes
  4. washwashed with 100 ml of 2 N sodium hydroxide solution and with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated down
  7. customThe brown, oily flask residue is chromatographed through a silica gel column with ethyl acetate/petroleum ether (20:80 to 50:50) as eluant
  8. customThe product obtained
  9. customis reacted further without any more purification

Sources & evidence

ORD record
ord-77dae159c9aa443f8d0e1d7de27194e2
Source dataset
uspto-grants-2014_03
Patent number
US08664232B2

Reaction notes

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