Hydrazine hydrate (1:1) → 6-(Pyrimidin-5-YL)hexan-1-amine

HRID 1583415Notes

Reaction equation

HRID 1583415 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH:4]=[N:3][CH:2]=1.O.NN>C(O)C>[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135575542-[6-(Pyrimidin-5-yl)hexyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 135575456-(Pyrimidin-5-YL)hexan-1-amineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 23.2 g of 2-[6-(5-pyrimidinyl)hexyl]-1H-isoindole-1,3-(2H)-dione and 14.6 ml of hydrazine hydrate in 320 ml of ethanol was heated to reflux for 3 hours. The cooled mixture was filtered and the filtrate was concentrated and dissolved in dichloromethne. The solution was washed with 5% sodium hydroxide, dried and evaporated to an oil which was evaportively distilled to yield 12.0 g (90%) of 5-pyrimidinehexanamine, bp 120°-128° C./0.6 mm.

Workup

  1. temperatureto reflux for 3 hours
  2. filtrationThe cooled mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutiondissolved in dichloromethne
  5. washThe solution was washed with 5% sodium hydroxide
  6. customdried
  7. customevaporated to an oil which
  8. distillationwas evaportively distilled

Sources & evidence

ORD record
ord-3f4c8bd853ef4606b58a558e7f5f961c
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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