Benzaldehyde → HCID 14547193, compound

HRID 974224Notes

Reaction equation

HRID 974224 reaction equation
[Cl:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:5]2[CH:6]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH:22](=O)C1C=CC=CC=1.Cl.[OH-].[Na+]>C(O)=O.O>[Cl:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:5]2[CH:6]([C:11]3[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=3)[CH2:7][N:8]([CH3:22])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13625428HCID 13625428, compound

Product 1

HCID 14547193HCID 14547193, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of benzazepine 3 (7.20 g, 19.6 mmol) in formic acid (2.3 g) was added 37% benzaldehyde (1.8 g). The mixture was heated to 90°-100° C. for four hours. After cooling the reaction mixture to room temperature, 4N hydrochloric acid solution (5.16 mL) was added. The mixture was condensed to dryness under reduced pressure. The residue was dissolved in water and then made basic with 25% sodium hydroxide solution. The mixture was extracted three times with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate. The solvent was evaporated to obtain a solid which was purified by column chromatography (silica gel; CH2Cl2 :MeOH:NH4OH;95:5:1) to give 4, 6.0 g (80%): mp 116°-118° C.; FT-IR (KBr)λ1500, 1380, 1270 and 1060 cm-1 ; 1H NMR (CDCl3)δd 7.65-7.35 and 7.21-6.90 (AA'BB',4H, ArH'), 7.13 (S, 1H, ArH #6), 6.38 (S, 1H, ArH #9), 4.40-4.10 (m, 1H, CH), 3.70 (S, 3H, OCH3), 3.10-2.45 (m, 6H, (CH2)3), 2.37 (S, 3H, NCH3). Anal. Calcd for C18H19BrCINO: C,H,N.

Workup

  1. temperatureThe mixture was heated to 90°-100° C. for four hours
  2. customcondensed to dryness under reduced pressure
  3. extractionThe mixture was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto obtain a solid which
  7. customwas purified by column chromatography (silica gel; CH2Cl2 :MeOH:NH4OH;95:5:1)
  8. customto give 4, 6.0 g (80%)

Sources & evidence

ORD record
ord-39fe37ed6e464e8399ab2bc0dc4e34c9
Source dataset
uspto-grants-1991_11
Patent number
US05068326

Reaction notes

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