Ammonia → HCID 28246448, compound

HRID 361604Notes

Reaction equation

HRID 361604 reaction equation
O[C@@H]([C@H](O)C(O)=O)C(O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C@H:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][NH:18]1.N>O>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C@H:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][NH:18]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86753649HCID 86753649, compound

Product 1

HCID 28246448HCID 28246448, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11.16 g of (R)-1-pyridin-2-yl-1,2,3,4-tetrahydro-isoquinoline (2S,3S)-2,3-dihydroxy-succinate (1:1) was dissolved in 100 ml of water and treated with 10 ml of a 25% aqueous ammonia solution. The mixture was extracted with 2×100 ml of diethyl ether. The combined organic phases were washed with 100 ml of water, dried over sodium sulfate and evaporated to dryness. The residue was distilled in a bulb-tube in order to give 6.35 g of (R)-1-pyridin-2-yl-1,2,3,4-tetrahydro-isoquinoline as a colorless oil, b.p. 135° C./0.15 mbar, which crystallized upon standing, m.p. 50°-52° C.

Workup

  1. extractionThe mixture was extracted with 2×100 ml of diethyl ether
  2. washThe combined organic phases were washed with 100 ml of water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. distillationThe residue was distilled in a bulb-tube in order

Sources & evidence

ORD record
ord-60348f716dce44c6bc709cc058290ee0
Source dataset
uspto-grants-1999_02
Patent number
US05866583

Reaction notes

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