4-Isopropylaniline → HCID 773658, compound

HRID 2109602Notes

Reaction equation

HRID 2109602 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 2N 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 2N 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-d9f2a12476d64f80b096e99c5c0d7411
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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