Hydrochloric Acid → HCID 20376329, compound

HRID 2052692Notes

Reaction equation

HRID 2052692 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.Cl.[CH3:22][O-:23].[Na+]>CN(C)C=O>[CH:22]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 12519122HCID 12519122, compound

Product 1

HCID 20376329HCID 20376329, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 15.7 g of 1-(2-amino-4-trifluoromethylphenyl)indoline.HCl in 75 ml of dry dimethylformamide, kept under N2, is immersed in an oil bath preheated to 100° C. After 5 minutes, 8.1 g of fresh, solid sodium methoxide is added in one portion. The mixture is quickly (15 minutes) brought to reflux, and kept at reflux an additional 45 minutes. The heating bath is then removed and when the internal temperature falls to 100° C., 300 ml of water is added in portions, with vigorous stirring. The product separates first as an oil which then solidifies. This material is filtered, washed with H2O, with alcohol, and dried to afford 1-(2-formamido-4-trifluoromethylphenyl)indoline, m.p. 135°-357° C.

Workup

  1. customis immersed in an oil bath
  2. custompreheated to 100° C
  3. custom(15 minutes)
  4. temperatureto reflux
  5. temperatureat reflux an additional 45 minutes
  6. customThe heating bath is then removed
  7. customfalls to 100° C.
  8. addition300 ml of water is added in portions, with vigorous stirring
  9. filtrationThis material is filtered
  10. washwashed with H2O, with alcohol
  11. customdried

Sources & evidence

ORD record
ord-ab6456e65b3a4ac2af3dfd4295f721e5
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

Loading…