Hydrazine hydrate (1:1) → 3-(2-Aminoethyl)-1H-indole-5-carboximidic acid

HRID 1414040Notes

Reaction equation

HRID 1414040 reaction equation
O.NN.C1(=O)[N:8](C(N)=O)[C:7](=O)[C:6]2=CC=CC=C12.O=C1C2C(=CC=CC=2)C(=O)N1CC[C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([C:40]([NH2:42])=[O:41])=[CH:35][CH:34]=2.CN1C(N)=NC(=O)C1.S([O-])([O-])(=O)=O>C(O)C.O>[NH2:8][CH2:7][CH2:6][C:39]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:40]([NH2:42])=[O:41])[CH:37]=2)[NH:32][CH:31]=1

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 13147563HCID 13147563, compoundHCID 20289470HCID 20289470, compoundHCID 22217699HCID 22217699, compound

Product 1

HCID 18093-(2-Aminoethyl)-1H-indole-5-carboximidic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent4×HCID 962WaterSolvent

Procedure

Hydrazine hydrate (30 ml) was added to the crude phthalimido carboxamide prepared in (ii) above (1.5 g) in ethanol (60 ml). The mixture was refluxed for 2.5 hours and cooled. The solvent was evaporated off and the residue stirred with 2 N sodium carbonate solution (60 ml) and the resulting solution was evaporated to dryness. The residue was extracted with ethanol and the combined extracts were evaporated to give a yellow solid that was dissolved in hot ethanol (45 ml) and treated with a solution of creatinine sulphate (1.6 g) in water (20 ml) and ethanol (10 ml). The solution obtained was diluted with ethanol to 85 ml. The title compound (1.8 g) precipitated as an off-white solid m.p. 205°-210° C.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. temperaturecooled
  3. customThe solvent was evaporated off
  4. customthe resulting solution was evaporated to dryness
  5. extractionThe residue was extracted with ethanol
  6. customthe combined extracts were evaporated
  7. customto give a yellow solid
  8. customThe solution obtained
  9. customThe title compound (1.8 g) precipitated as an off-white solid m.p. 205°-210° C.

Sources & evidence

ORD record
ord-e39fa1aee398421d82001c133b1f623b
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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