Anthranilic Acid → HCID 66753771, compound

HRID 1454950Notes

Reaction equation

HRID 1454950 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.N(OCCC(C)C)=O>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]triazine-3-carboxylate (Sagi et al., Heterocycles 1989, 29, 2253) is refluxed in 20 ml of dioxane. Then 8.22 g anthranilic acid and 7.02 g isoamyl nitrite, in each case dissolved in 20 ml dioxane, are simultaneously added dropwise within 25 minutes using two dropping funnels. The reaction mixture is refluxed for a further 30 minutes. For working up the cooled dark 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 further reacted without any further purification.

Workup

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

Sources & evidence

ORD record
ord-1f3e966f47c0487482c451ba49d44ef2
Source dataset
uspto-grants-2009_01
Patent number
US07482337B2

Reaction notes

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