Water → HCID 13055798, compound

HRID 1702619Notes

Reaction equation

HRID 1702619 reaction equation
C([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]([CH3:14])[CH2:5]1)(=O)C.C(O[CH:18]=[C:19]([C:25]([O:27]CC)=O)[C:20]([O:22]CC)=[O:21])C.O.[OH-].[Na+]>C(O)(=O)C>[CH3:14][CH:6]1[N:7]2[CH:18]=[C:19]([C:20]([OH:22])=[O:21])[C:25](=[O:27])[C:9]3[C:8]2=[C:13]([CH:12]=[CH:11][CH:10]=3)[NH:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 13393699HCID 13393699, compound

Product 1

HCID 13055798HCID 13055798, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.0894 mole (1.7 g) of optically purified (+) 1-acetyl-3-methyl-1,2,3,4-tetrahydroquinoxaline and 0.009 mole (1.9 g) diethyl ethoxymethylenemalonate was heated over one hour to 200° C. and maintained at that temperature for 1.5 hours. After cooling, 5 g of polyphosphoric acid were added and the mixture was heated at 120° C. until foaming stops. The mixture was stirred into water and the solution was made strongly basic with 25 percent sodium hydroxide. The solution was stirred and heated on a steam bath for one hour, then neutralized with acetic acid. Cooling, followed by filtration provided an olive green solid R(+) 2,3-dihydro-3-methyl-7-oxopyrido-[1,2,3-de]quinoxaline-6- carboxylic acid, m.p. >250° C. Analysis: Calculated for C13H12N2O3 : %C, 63.9; %H, 5.0; %N, 11.5; Found: %C, 63.4; %H, 5.0; %N, 11.6. Optical rotation [α]21 D = 93±3° (C=0.594, N,N-dimethylformamide:ethanol, 1/1).

Workup

  1. temperaturewas heated over one hour to 200° C.
  2. temperaturemaintained at that temperature for 1.5 hours
  3. temperatureAfter cooling
  4. temperatureheated on a steam bath for one hour
  5. temperatureCooling
  6. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-606f571efe7442cabc83ec2a707c6310
Source dataset
uspto-grants-1982_09
Patent number
US04348521

Reaction notes

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