Triethylamine → HCID 53688362, compound

HRID 1106412Notes

Reaction equation

HRID 1106412 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[NH2:21])=[CH:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[Cl-].C([O:33][C:34](=O)[C:35](O)=[O:36])C>O1CCCC1>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:12]3[C:13](=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)[NH:21][C:34](=[O:33])[C:35]2=[O:36])=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 23618337Oxalic acid monoethylester chloride2×HCID 544420634-(2-Amino-4-nitrophenylamino)benzoic acid ethyl ester

Product 1

HCID 53688362HCID 53688362, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At a bath temperature of +4° C., under argon and with exclusion of moisture, 582 mg (2.3 mmol) of 4-(2-amino-4-nitrophenylamino)benzoic acid ethyl ester is combined with 488 mg (4.8 mmol) of triethylamine in 27 ml of dry tetrahydrofuran. A solution of 659 mg (4.8 mmol) of oxalic acid ethyl ester chloride and 8 ml of dry tetrahydrofuran is added dropwise to this batch and stirred for 2 hours at room temperature. The mixture is then combined with 0.2 ml of triethylamine and 0.1 ml of oxalic acid ethyl ester chloride, and agitated for one hour at room temperature. The batch is filtered, and the filtrate is concentrated and distributed in water/ethyl acetate. The organic phase is concentrated. The residue is refluxed for 2 hours at the bath temperature in 25 ml of 1N hydrochloric acid and 25 ml of ethanol. The thus-precipitated product is suctioned off, washed with water, and dried, yielding 220 mg of 4-(6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)benzoic acid ethyl ester (further processed without purification).

Workup

  1. stirringagitated for one hour at room temperature
  2. filtrationThe batch is filtered
  3. concentrationthe filtrate is concentrated
  4. concentrationThe organic phase is concentrated
  5. temperatureThe residue is refluxed for 2 hours at the bath temperature in 25 ml of 1N hydrochloric acid
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0ca8dcd16d204df08dc3800d1ed77a0a
Source dataset
uspto-grants-2000_05
Patent number
US06057304

Reaction notes

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