4-Chloro-2-methoxypyridine-3-carbaldehyde → HCID 66687188, compound

HRID 920500Notes

Reaction equation

HRID 920500 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:12])[NH:6][C:5]2=[O:13].[Cl:14][C:15]1[C:20]([CH:21]=O)=[C:19]([O:23][CH3:24])[N:18]=[CH:17][CH:16]=1>CO.CC(O)=O.O>[Cl:14][C:15]1[CH:16]=[CH:17][N:18]=[C:19]([O:23][CH3:24])[C:20]=1[C:21]1[NH:11][C:10]2=[CH:9][C:8]3[C:7](=[O:12])[NH:6][C:5](=[O:13])[C:4]=3[CH:3]=[C:2]2[N:1]=1

Participants

5

Reactant 2

HCID 534079284-Chloro-2-methoxypyridine-3-carbaldehydeHCID 58188525HCID 58188525, compound

Product 1

HCID 66687188HCID 66687188, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10129899Acetic acid methanolSolvent

Procedure

5,6-Diaminoisoindoline-1,3-dione (2.88 g, 16.26 mmol) and 4-chloro-2-methoxynicotinaldehyde (2.79 g, 16.26 mmol) were suspended in MeOH/HOAc (200 mL, 3/1 v/v) at rt under air. The reaction mixture was stirred under air overnight and diluted with 200 mL of water. The solid was filtered, washed with acetone and recrystallized from hot EtOAc to give a pale-yellow solid product, 4.67 g, 87.5% yield. MS: 329.0 [M+H]+. 1H NMR (DMSO-d6, 500 MHz): δ 13.23 (s, 1H), 8.36 (d, 1H, J=5.5 Hz), 8.02 (S, 2H), 7.39 (d, 1H, J=6.0 Hz), 3.89 (s, 3H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with acetone
  3. customrecrystallized from hot EtOAc
  4. customto give a pale-yellow solid product, 4.67 g, 87.5% yield

Sources & evidence

ORD record
ord-c8f3418abd224122bb4f13aed5dfa564
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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