Hydrochloric Acid → 3-(1H-pyrazol-4-yl)propan-1-amine dihydrochloride

HRID 66392Notes

Reaction equation

HRID 66392 reaction equation
C1(=O)[NH:5]C(=O)C2=CC=CC=C12.[ClH:12].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H]([N:43]5[CH:48]=[C:47]([C:49]([NH2:51])=O)[CH2:46][CH:45]=[CH:44]5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1>>[ClH:12].[ClH:12].[NH2:5][CH2:44][CH2:45][CH2:46][C:47]1[CH:48]=[N:43][NH:51][CH:49]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6809PhthalimideHCID 439153Nadh

Product 1

HCID 227549333-(1H-pyrazol-4-yl)propan-1-amine dihydrochloride

Conditions

Temperature
4 °C

Procedure

This phthalimide intermediate (8.0 gram, 0.03 mole) was refluxed in 100 ml. of 6 normal hydrochloric acid overnight. The clear solution was cooled to 4° C., phthalic acid removed by filtration, and the filtrate evaporated to dryness to give a product which, after recrystallization from a mixture of ethanol and ethyl ether, amounted to 4.4 grams of a white solid identified as 4-(3-aminopropyl)-pyrazole dihydrochloride, melting point 189°-190° C. This pyrazole compound could be coupled to the activated dextran by reaction of the terminal amino group, but the resulting affinity resin, in which the coupling arm had a length of only 6 Angstrom units, had poor binding capacity for the binary complex of alcohol dehydrogenase and NAD.

Workup

  1. customphthalic acid removed by filtration
  2. customthe filtrate evaporated to dryness
  3. customto give a product which
  4. customafter recrystallization
  5. additionfrom a mixture of ethanol and ethyl ether
  6. customThis pyrazole compound could be coupled to the activated dextran by reaction of the terminal amino group

Sources & evidence

ORD record
ord-2019574de9bf4a3f9f66054b1f3086e5
Source dataset
uspto-grants-1978_12
Patent number
US04131727

Reaction notes

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