Hydrochloric Acid → HCID 18986940, compound

HRID 2397072Notes

Reaction equation

HRID 2397072 reaction equation
[CH:1]1[C:11]2C=CC3C=CC=CC=3[CH:6]([C:16]([NH:27][C:28](=O)C)(C(OCC)=O)C(OCC)=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-:31].[Na+].Cl.[CH3:34][OH:35]>O>[CH:11]1[C:5]2[CH:4]=[CH:6][C:5]3[CH:11]=[CH:1][CH:2]=[CH:3][C:4]=3[CH:16]([NH:27][CH2:28][C:34]([OH:35])=[O:31])[C:6]=2[CH:3]=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18986938HCID 18986938, compound

Product 1

HCID 18986940HCID 18986940, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of diethyl 2-(5H-dibenzo[a,d]cyclohepten-5-yl)-2-acetamidomalonate (20.2g, Example 1b) and sodium hydroxide (4g) in methanol (75ml) and water (75ml) was heated to reflux for 8h. To the cooled solution was added 1M-HCl until pH=6. The solution was concentrated in vacuo and acidified to pH=2 by addition of 1M-HCl. The solid which formed was collected by filtration and heated together with 6M-HCl for 3h at 100° C. The cooled solution was filtered and the residue dissolved in hot water, refiltered and to the filtrate was added aqueous ammonia until pH 7-8. The solid which formed on cooling to room temperature was collected by filtration and dried in vacuo to give 5H-dibenzo[a,d]cyclohepten-5-ylglycine. 1H NMR (360MHz, d4MeOH), δ 4.08-4.12 (1H, m), 4.35-4.39 (1H, m), 7.0-7.11 (2H, m), 7.24-7.30 (3H, m), 7.34-7.45 (5H, m).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8h
  3. concentrationThe solution was concentrated in vacuo
  4. additionacidified to pH=2 by addition of 1M-HCl
  5. customThe solid which formed
  6. filtrationwas collected by filtration
  7. filtrationThe cooled solution was filtered
  8. dissolutionthe residue dissolved in hot water
  9. additionwas added aqueous ammonia until pH 7-8
  10. customThe solid which formed
  11. temperatureon cooling to room temperature
  12. filtrationwas collected by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-70f95ee931b24d82a37e43fc54f504ec
Source dataset
uspto-grants-1996_02
Patent number
US05495047

Reaction notes

Loading…