Formic Acid → Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate

HRID 717818Notes

Reaction equation

HRID 717818 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]([Cl:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:4]=1.[CH:21](O)=[O:22]>>[Cl:13][C:12]1[C:3]([CH2:2][NH:1][CH:21]=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 58515976Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

Product 1

HCID 58515924Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate

Conditions

Temperature
90 °C

Procedure

Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate (1.1 g, 3.7 mmol) was stirred in formic acid (10 mL) and heated to 90° C. for 10 hours. Evaporation gave the crude material which was contaminated with the corresponding dechlorinated byproduct (1.1 g, quantitative). LCMS calculated for C15H13ClFN2O3 (M+H)+: m/z=323.1. found: 322.9.

Workup

  1. customEvaporation

Sources & evidence

ORD record
ord-4d9d436cc8cd400e9d781a09a9ec1422
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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