Methane → 2-n-Hexyl-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

HRID 568813Notes

Reaction equation

HRID 568813 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](O)=O.C>C(O)C>[CH2:16]([C:15]1[NH:11][C:10]2[CH:9]=[C:8]3[NH:7][C:6](=[O:12])[C:5]([CH3:14])([CH3:13])[C:4]3=[CH:3][C:2]=2[N:1]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 297MethaneHCID 8094Heptanoic AcidHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 1784424832-n-Hexyl-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to Example 11, from 0.48 g. 5,6-diamino-3,3-dimethylindolin-2-one and 0.36 g. oenanthic acid, after heating with 4.5 g. polyphosphoric acid for 30 minutes at a bath temperature of 200° C., there is obtained 0.7 g. of crude product which is dissolved in 35 ml. ethanol, treated with active charcoal, filtered and the clear filtrate evaporated in a vacuum. The evaporation residue, after trituration with diethyl ether, gives 0.37 g. of the title compound in the form of the monohydrate; m.p. 233°-234° C.

Workup

  1. customthere is obtained 0.7 g
  2. dissolutionof crude product which is dissolved in 35 ml
  3. filtrationfiltered
  4. customthe clear filtrate evaporated in a vacuum
  5. customThe evaporation residue, after trituration with diethyl ether, gives 0.37 g

Sources & evidence

ORD record
ord-c38c06f361c249b4a27abb52c676b02c
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

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