Hydrochloric Acid → HCID 22917218, compound

HRID 1984833Notes

Reaction equation

HRID 1984833 reaction equation
[NH2:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[CH2:18]([O:20][C:21](=[O:29])[CH:22](Br)[C:23](OCC)=[O:24])[CH3:19].Cl>C(O)C.O>[CH2:18]([O:20][C:21]([C:22]1[C:23](=[O:24])[NH:1][C:2]2[C:3](=[CH:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=2)[N:4]=1)=[O:29])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69637Diethyl bromomalonateHCID 1534044-Methoxy-o-phenylenediamine

Product 1

HCID 22917218HCID 22917218, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-methoxy aniline (5.0 g, 36.2 mmol) was dissolved in 50 mL of ethanol and triethylamine (5.08 mL, 69.1 mmol) added. The mixture was cooled to 0° C. and diethylbromomalonate (8.02 mL, 47.0 mmol) in 8 mL of ethanol was added dropwise over 30 minutes. Mixture is stirred at 0° C. for 30 minutes and 16 h at room temperature. The resulting solid was isolated and stirred in 200 mL water and 50 mL 1N HCl for 1 h. The solid was filtered, suspended in toluene and evaporated to dryness to give the 6-methoxy-3-oxo-3,4-dihydro-quinoxaline-2-carboxylic acid ethyl ester as a solid (5.2 g).

Workup

  1. customThe resulting solid was isolated
  2. filtrationThe solid was filtered
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-6557c1457041489c967a06401964c820
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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