Methane → HCID 70473491, compound

HRID 435119Notes

Reaction equation

HRID 435119 reaction equation
C([NH:4][CH2:5][C:6]1[C:17]2=[C:18]3[N:13]([CH:14]([CH3:19])[CH2:15][CH2:16]2)[CH:12]=[C:11]([C:20]([O:22]CC)=[O:21])[C:10](=[O:25])[C:9]3=[CH:8][CH:7]=1)(=[O:3])C.Cl.C([O-])(=O)C.[Na+].C>O>[OH2:3].[NH2:4][CH2:5][C:6]1[C:17]2=[C:18]3[N:13]([CH:14]([CH3:19])[CH2:15][CH2:16]2)[CH:12]=[C:11]([C:20]([OH:22])=[O:21])[C:10](=[O:25])[C:9]3=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 20490860HCID 20490860, compound

Product 1

HCID 70473491HCID 70473491, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product ethyl 8-acetamidomethyl-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate (1.0 g) from Example 6 was mixed with 25 ml of 6 N hydrochloric acid, and the mixture was heated at reflux for two hours. The mixture was evaporated to dryness, and the residue was triturated with isopropyl alcohol. The solid obtained was dissolved in 20 ml of water. One gram of sodium acetate was added, and the mixture was treated with decolorizing charcoal and filtered. The volume of the solution was reduced to 5 ml, and 5 ml of isopropyl alcohol was added. Seeding was used to provide white crystals of 8-aminomethyl-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrate, m.p. 228°-250° C. (dec.). Analysis: Calculated for C15H16N2O3.1/2H2O: %C, 64.0; %H, 6.1; %N, 10.0; Found: %C, 63.9, %H, 5.9; %N, 9.7. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for two hours
  3. customThe mixture was evaporated to dryness
  4. customthe residue was triturated with isopropyl alcohol
  5. customThe solid obtained
  6. filtrationfiltered
  7. additionwas added

Sources & evidence

ORD record
ord-d0c00973263148c7a793f2ea191b6c2b
Source dataset
uspto-grants-1983_08
Patent number
US04400386

Reaction notes

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