Hydrochloric Acid → HCID 15557214, compound

HRID 1763843Notes

Reaction equation

HRID 1763843 reaction equation
[NH2:1][C:2]1[N:3]([CH3:17])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:18]([O:20]C(Cl)=O)C.Cl>N1C=CC=CC=1>[CH3:17][N:3]1[C:2]2[NH:1][C:18](=[O:20])[C:16]3[C:11]([C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)=[CH:12][CH:13]=[CH:14][CH:15]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformate2×HCID 155572071-Methyl-3-phenyl-1H-indol-2-amine

Product 1

HCID 15557214HCID 15557214, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2.59 g (0.01 mole) of 2-amino-1-methyl-3-phenylindole in 15 ml of pyridine, 2.84 g (0.026 mole) of ethylchlorocarbonate is added. The reaction mixture is heated to 75° C. for about 2 hours, allowed to cool and 2.84 g more of ethylchlorocarbonate is added. The reaction mixture, heated for a further 3 hours, is then poured into about 200 ml of aqueous 10% HCl solution, the product is extracted with ethyl ether and the organic layer washed with water. The resulting etheral solution, dried over sodium sulfate, is concentrated to a volume of about 30 ml, 20 ml of hexane is added and the solution is once again concentrated to 35 ml. The product, 2.3 g of 1-methyl-3-phenylindole-2-carbamic acid ethyl ester, is thus crystallized; (m.p. 159°-161° C.; yield 80%). A quantity of 1.4 g of the so obtained carbamate is heated to 270° C. for 15 minutes and the residue crystallized from dimethylformamide, yielding 1.15 g of 7-methylindolo[2,3-c]isoquinolin-5(6H)-one. M.p. 350° C. (with decomposition). Yield 95%.

Workup

  1. temperatureto cool
  2. temperatureThe reaction mixture, heated for a further 3 hours
  3. extractionthe product is extracted with ethyl ether
  4. washthe organic layer washed with water
  5. dry with materialThe resulting etheral solution, dried over sodium sulfate
  6. concentrationis concentrated to a volume of about 30 ml, 20 ml of hexane
  7. additionis added
  8. concentrationthe solution is once again concentrated to 35 ml
  9. customThe product, 2.3 g of 1-methyl-3-phenylindole-2-carbamic acid ethyl ester, is thus crystallized
  10. temperatureA quantity of 1.4 g of the so obtained carbamate is heated to 270° C. for 15 minutes
  11. customthe residue crystallized from dimethylformamide

Sources & evidence

ORD record
ord-de6415eca8ad4e958671a67194811eb2
Source dataset
uspto-grants-1978_09
Patent number
US04113731

Reaction notes

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