Triethylamine → HCID 14535906, compound

HRID 1904922Notes

Reaction equation

HRID 1904922 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([CH3:12])[CH2:5][CH:6]2[Cl:11].C(N(CC)CC)C.[Cl:20][C:21]1[N:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>O1CCCC1>[Cl:20][C:21]1[C:22]([C:23]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]([CH3:12])[CH2:5][CH:6]3[Cl:11])=[O:24])=[CH:26][CH:27]=[CH:28][N:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 20036421HCID 20036421, compound

Product 1

HCID 14535906HCID 14535906, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g (5.5 mmol) of 4-amino-1-chloro-3-methylindane and 0.7 g (6.9 mmol) of triethylamine in 15 ml of tetrahydrofuran was added 1.1 g (6.2 mmol) of 2-chloronicotinic acid chloride under ice cooling, and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over Glauber's salt and then concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=2/1) to obtain 1.3 g of white crystals (Compound No. 6 shown in Table 2) in a yield of 75%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over Glauber's salt
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel chromatography (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-bbdceb56e45c45669c0dc43470ea12de
Source dataset
uspto-grants-1989_06
Patent number
US04840959

Reaction notes

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