Ammonia → HCID 10685153, compound

HRID 2210889Notes

Reaction equation

HRID 2210889 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.C(N(CC)CC)C.[Cl:19][C:20]([Cl:25])([Cl:24])[C:21](Cl)=[O:22].N>C(Cl)Cl>[Cl:19][C:20]([Cl:25])([Cl:24])[C:21]([NH:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1)=[O:22]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 106543695,6,7,8-tetrahydroquinolin-3-amine

Product 1

HCID 10685153HCID 10685153, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 130 ml of methylene chloride are added 12.69 g of Compound 1 obtained in the above step (1) and 2.4 ml of triethylamine, and a solution of 10.5 ml of trichloroacetyl chloride in 30 ml of methylene chloride is dropwise added with ice cooling and under stirring over a period of 7 minutes. The reaction mixture is stirred at room temperature for 20 minutes, mixed with saturated saline, made weakly alkaline with aqueous ammonia and the organic layer is separated. The aqueous layer is shaken with methylene chloride. The organic layers are combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to remove the solvent. The residue is chromatographed on a silica gel column, eluting with 10% methanol/methylene chloride. The product is recrystallized from ethyl acetate to give 24.21 g of the titled compound 2. Yield: 96% mp.: 157° to 159° C.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 20 minutes
  2. additionmixed with saturated saline
  3. customthe organic layer is separated
  4. stirringThe aqueous layer is shaken with methylene chloride
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto remove the solvent
  9. customThe residue is chromatographed on a silica gel column
  10. washeluting with 10% methanol/methylene chloride
  11. customThe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-348784efafd24714a1129d72008e27d2
Source dataset
uspto-grants-1995_10
Patent number
US05461062

Reaction notes

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