Dimethylformamide → HCID 16791679, compound

HRID 1859658Notes

Reaction equation

HRID 1859658 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[N+:18]([O-])=O.CN(C=O)C.[Cl:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30]>CCCCCC>[NH2:18][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[O:8][CH3:7])[C:13]([NH:30][C:29]1[CH:31]=[CH:32][CH:33]=[C:27]([Cl:26])[CH:28]=1)=[O:15]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 79323-ChloroanilineHCID 65578Oxalyl chlorideHCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 16791679HCID 16791679, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (3.0 mL, 34.39 mmol), 4-methoxy-3-nitrobenzoic acid (5.00 g, 25.36 mmol), DMF (0.5 mL, 6.46 mmol), and 3-chloroaniline (5.4 mL, 51.05 mmol). The reduction was performed as described but using DMF as the solvent to afford the product (2.29 g) after trituration in hexane; m.p. 144-146° C. after recrystallization from ethyl acetate.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7e3427768634428d8f2bc34a7f589f16
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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