Pyridine → 2-chloro-N-(1,1-dimethylindan-4-yl)-pyridine-3-carboxamide

HRID 1904921Notes

Reaction equation

HRID 1904921 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2([CH3:12])[CH3:11].N1C=CC=CC=1.[Cl:19][C:20]1[N:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>C(OCC)(=O)C>[Cl:19][C:20]1[C:21]([C:22]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3([CH3:12])[CH3:11])=[O:23])=[CH:25][CH:26]=[CH:27][N:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27745412-Chloronicotinoyl chlorideHCID 131156151,1-Dimethyl-2,3-dihydro-1H-inden-4-amine

Product 1

HCID 145359012-chloro-N-(1,1-dimethylindan-4-yl)-pyridine-3-carboxamideYield 83.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 200 mg (1.2 mmol) of 4-amino-1,1-dimethylindane and 0.15 g (1.9 mmol) of pyridine in 15 ml of ethyl acetate was added 0.24 g (1.4 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 white residue was recrystallized with hexane to obtain 300 mg of white crystals (Compound No. 1 shown in Table 2). The yield was 80.4%.

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 white residue was recrystallized with hexane

Sources & evidence

ORD record
ord-377c9a9fa58d45b78201ef89366de76d
Source dataset
uspto-grants-1989_06
Patent number
US04840959

Reaction notes

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