Ammonia → HCID 18596257, compound

HRID 745520Notes

Reaction equation

HRID 745520 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:14][C@H:13]3[C@@H:8]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:15][CH2:16][CH3:17])[CH2:7][C:6]=2[N:18]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].N>C(Cl)(Cl)Cl.CO>[C:25]([NH:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:14][C@H:13]3[C@@H:8]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:15][CH2:16][CH3:17])[CH2:7][C:6]=2[N:18]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 7918Acetic Anhydride2×HCID 18596256HCID 18596256, compound

Product 1

HCID 18596257HCID 18596257, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution was prepared containing 0.75 g of trans-(±)-2-amino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline in 20 ml. of pyridine and 0.34 g. of acetic anhydride was added thereto in dropwise fashion. The reaction mixture was heated to reflux temperature under a nitrogen blanket overnight. TLC at this point in time indicated that starting material was still present; therefore, about 1.5 ml. more acetic anhydride were added and the reaction mixture again heated to reflux temperature under a nitrogen blanket. TLC, using a 9:1 chloroform/methanol solvent system containing ammonia, indicated that the reaction had gone largely toward completion but that some starting material was still present. The reaction mixture was therefore concentrated in vacuo and the resulting residue triturated in hot ethyl acetate. On cooling, crystals formed which were isolated by filtration. Thirty-four hundredths grams of trans-(±)-2-acetylamino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline were obtained; molecular ion at 288; nmr and infrared spectra were in comformance with the proposed structure.

Workup

  1. customA solution was prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux temperature under a nitrogen blanket overnight
  4. temperaturethe reaction mixture again heated
  5. temperatureto reflux temperature under a nitrogen blanket
  6. concentrationThe reaction mixture was therefore concentrated in vacuo
  7. customthe resulting residue triturated in hot ethyl acetate
  8. temperatureOn cooling
  9. customcrystals formed which
  10. customwere isolated by filtration

Sources & evidence

ORD record
ord-342ac7921c0344bd8d863be573d8d773
Source dataset
uspto-grants-1986_07
Patent number
US04599339

Reaction notes

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