Dimethylamine → HCID 12519129, compound

HRID 2052691Notes

Reaction equation

HRID 2052691 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.CN(C)[CH:21]=[O:22].C[O-].[Na+].CNC>O>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[NH:2][CH:21]=[O:22])[CH2:10][CH2:11]2

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 12519121HCID 12519121, compound

Product 1

HCID 12519129HCID 12519129, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture, under N2, of 24.3 g of 1-(2-amino-phenyl)-5-chloroindoline hydrochloride, of Example 5, and 150 ml of dry dimethylformamide (DMF) is immersed in a 100° C. pre-heated oil bath. Solution occurs at 60° C. when 14.4 g of solid sodium methoxide is added in one portion. The mixture is rapidly heated to reflux and kept there for 45 minutes during which dimethylamine evolves copiously. The reaction mixture is then treated, in portions and without further heating, with 2 liters of water to precipitate the product as an oil. The water is removed by decantation. The oil is taken up in chloroform, extracted with H2O, with 3N--HCl, once again with H2O, dried over sodium sulfate and concentrated to a hard glass. This is dissolved in hot benzene (charcoal) to which hexane is added. The solid of 5-chloro-1-(2-formamidophenyl)indoline, m.p. 126°-129° C. is collected.

Workup

  1. customis immersed in a 100° C.
  2. temperaturepre-heated oil bath
  3. customoccurs at 60° C.
  4. additionis added in one portion
  5. temperatureThe mixture is rapidly heated
  6. temperatureto reflux
  7. customto precipitate the product as an oil
  8. customThe water is removed by decantation
  9. extractionextracted with H2O, with 3N
  10. dry with materialHCl, once again with H2O, dried over sodium sulfate
  11. concentrationconcentrated to a hard glass
  12. dissolutionThis is dissolved in hot benzene (charcoal) to which hexane
  13. additionis added
  14. customThe solid of 5-chloro-1-(2-formamidophenyl)indoline, m.p. 126°-129° C. is collected

Sources & evidence

ORD record
ord-7bac528fe8e748629e0b2f61d41c1ed4
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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