N-Methylformanilide → HCID 20394938, compound

HRID 261446Notes

Reaction equation

HRID 261446 reaction equation
Br[C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]2[O:19][CH2:20][O:21][C:3]=12.C([Li])CCC.CN([CH:35]=[O:36])C1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[CH:35]([C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]2[O:19][CH2:20][O:21][C:3]=12)=[O:36]

Participants

6

Reactant 3

HCID 66737N-MethylformanilideHCID 13187661HCID 13187661, compoundHCID 178418339Butyllithium

Product 1

HCID 20394938HCID 20394938, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.8 g (0.0225 mole) of 6-bromo-7,8-methylenedioxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine in toluene was added to a mixture of 2.2 ml (6.07 mole) of butyl lithium diluted with 100 ml of ethyl ether at -78°. Then, 10 ml of N-methylformanilide was added. After stirring for 1 hour at -78°, the cooling bath was removed and 100 ml of 10% hydrochloric acid was added. After stirring for 15 minutes, the layers were separated. The ether layer was dried and evaporated. The residue was dissolved in ethyl acetate then extracted by aqueous sodium bisulfite. The aqueous layer was removed, washed with ether and made basic with solid carbonate. After extraction with ethyl ether the extracts were evaporated. The residue was heated in 6 N hydrochloric acid for 1 hour. The solution was made basic and the product extracted into chloroform. After purification over silica with 5% methanol-chloroform, 6-formyl-7,8-methylenedioxy-1-phenyl-2,3,4,5-tetrahydro- 1H-3-benzazepine was obtained as an oil.

Workup

  1. customthe cooling bath was removed
  2. addition100 ml of 10% hydrochloric acid was added
  3. stirringAfter stirring for 15 minutes
  4. customthe layers were separated
  5. dry with materialThe ether layer was dried
  6. customevaporated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. extractionthen extracted by aqueous sodium bisulfite
  9. customThe aqueous layer was removed
  10. washwashed with ether
  11. extractionAfter extraction with ethyl ether the extracts
  12. customwere evaporated
  13. temperatureThe residue was heated in 6 N hydrochloric acid for 1 hour
  14. extractionthe product extracted into chloroform
  15. customAfter purification over silica with 5% methanol-chloroform

Sources & evidence

ORD record
ord-2b6345addc564aa0b812f4028ee98aff
Source dataset
uspto-grants-1979_08
Patent number
US04165372

Reaction notes

Loading…