4-Isopropylaniline → HCID 773658, compound

HRID 1815180Notes

Reaction equation

HRID 1815180 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:11]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)([CH3:13])[CH3:12].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.C(Cl)CCl>[Cl:1][C:2]1[C:3]([C:4]([NH:18][C:17]2[CH:19]=[CH:20][C:14]([CH:11]([CH3:13])[CH3:12])=[CH:15][CH:16]=2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 74644-IsopropylanilineHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 81531Diisopropylethylamine

Product 1

HCID 773658HCID 773658, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-chloronicotinic acid (6.3 g) and 4-isopropylaniline (5.26 ml) and DIEA (10 ml) in CH2Cl2 (200 ml) was added EDC (10 g) and HOBt (5.4 g). The reaction was stirred at RT overnight and washed with 2 N NaOH (100 ml), H2O (250 ml) and brine (100 ml). The organic layer was dried over Na2SO4 and evaporated to give (2-chloro-3-pyridyl)-N-(4-isopropylphenyl)-carboxamide.

Workup

  1. washwashed with 2 N NaOH (100 ml), H2O (250 ml) and brine (100 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-3d8e710db31d4353a769097016bfdc32
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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