Water → HCID 86729558, compound

HRID 2280564Notes

Reaction equation

HRID 2280564 reaction equation
[Cl:1][C:2]1[C:11]([C:12](Cl)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[N:20][CH:21]=1.N1C=CC=CC=1.O>C(Cl)Cl>[Cl:1][C:2]1[C:11]([C:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[N:20][CH:21]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27946652-chloroquinoline-3-carbonyl chlorideHCID 12457877Methyl 5-aminopyridine-2-carboxylate

Product 1

HCID 86729558HCID 86729558, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloroquinoline-3-carbonyl chloride (2.72 g, 12.04 mmol) in methylene chloride (37.7 mL) was added dropwise to a mixture of methyl 5-aminopyridine-2-carboxylate (1.83 g, 12.04 mmol), pyridine (2.9 mL, 36.12 mmol) and methylene chloride (25.1 mL) at 0° C. The mixture was stirred and allowed to warm up to room temperature over 1.5 hours. To the reaction slurry, water (30 mL) was added and a precipitate formed. The solid was filtered, washed with water (2×30 mL), hexanes (2×50 mL), and a small amount of dichloromethane. The solid from the filtrate was isolated and washed with water (1×15 mL) and hexanes (1×20 mL). This solid obtained was dried in the vacuum oven to yield methyl 5-(2-chloroquinoline-3-carboxamido)picolinate (3 g, 73%). ESI-MS m/z calc. 341.06, found 342.2 (M+1)+; Retention time: 1.18 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 11.36 (s, 1H), 8.95 (d, J=2.5 Hz, 1H), 8.85 (s, 1H), 8.42 (dd, J=8.6, 2.5 Hz, 1H), 8.21-8.12 (m, 2H), 8.07 (dd, J=8.6, 1.1 Hz, 1H), 8.02-7.89 (m, 1H), 7.82-7.72 (m, 1H), 3.89 (s, 3H) ppm.

Workup

  1. customa precipitate formed
  2. filtrationThe solid was filtered
  3. washwashed with water (2×30 mL), hexanes (2×50 mL)
  4. customThe solid from the filtrate was isolated
  5. washwashed with water (1×15 mL) and hexanes (1×20 mL)
  6. customThis solid obtained
  7. customwas dried in the vacuum oven

Sources & evidence

ORD record
ord-afca8096305e4c07b833b431006b3422
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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