Dicyclohexylcarbodiimide → Ethyl 6-chloronicotinate

HRID 1663464Notes

Reaction equation

HRID 1663464 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.ClC([O-])=O.O=S(Cl)Cl.[C:19]1(OC(Cl)=O)C=CC=C[CH:20]=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.N=C=N.C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.ON1C(=O)CCC1=O>C(O)C.CN1C(=O)CCC1.CN(C=O)C.ClCCCl.C(Cl)Cl>[CH2:19]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1)[CH3:20]

Participants

16

Reactant 10

HCID 10868DicyclohexylcarbodiimideHCID 15891Phenyl chloroformateHCID 24386Thionyl ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 757711-HydroxybenzotriazoleHCID 792226-Chloronicotinic acidHCID 80170N-HydroxysuccinimideHCID 821294-Nitrophenyl chloroformateHCID 160435CarbodiimideHCID 21226386Carbonochloridate

Product 1

HCID 2799611Ethyl 6-chloronicotinate

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolvent2×HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Chloronicotinic acid 51 is activated by reacting with a chloroformate activating agent such as SOCl2, phenylchloroformate, or p-nitrophenyl chloroformate, or a carbodiimide activating agent such as CDI, DCC, or EDC in the presence of HOBt and N-hydroxysuccinimide in a polar aprotic solvent such as CH2Cl2, 1,2-dichloroethane, DMF, or NMP, and heating. An alcohol such as ethanol is then added to form 6-chloronicotinic acid ethyl ester 71.

Sources & evidence

ORD record
ord-9240b898d7294e04b584780b7beb78a1
Source dataset
uspto-grants-2011_10
Patent number
US08034950B2

Reaction notes

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