2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13037307, compound

HRID 1085441Notes

Reaction equation

HRID 1085441 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH3:19])[NH:10][C:9]=2[CH2:8][NH:7]1)=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[C:15]([CH3:19])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54562140HCID 54562140, compound

Product 1

HCID 13037307HCID 13037307, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

2.58 g of 5-methyl-1,2,3,4-tetrahydro-β-carbolin-3-carboxylic acid ethyl ester is dissolved in 40 ml of absolute toluene, cooled to 15° C., 2.72 g of dichlorodicyanobenzoquinone is added thereto and the whole is stirred for 1 hour at this temperature. The mixture is then diluted with ethyl acetate, extracted several times by shaking with dilute ammonia and then with saturated common salt solution, dried over calcium sulphate and concentrated in vacuo. Chromatography on silica gel with a chloroform-ethanol gradient yields 1.56 g of 5-methyl-β-carbolin-3-carboxylic acid ethyl ester of melting point 221°-223° C. (decomposition).

Workup

  1. extractionextracted several times
  2. stirringby shaking with dilute ammonia
  3. dry with materialwith saturated common salt solution, dried over calcium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4cb2fd6ed804f89b49f1053475140b3
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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