o-Amino-N-(2-chloro-3-pyridyl)benzamide → HCID 13933779, compound

HRID 569735Notes

Reaction equation

HRID 569735 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:19]1[C:26]2([C:27](Cl)=[O:28])[N:22]([CH2:23][CH2:24][CH2:25]2)[CH2:21][CH2:20]1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:27]([C:26]23[CH2:25][CH2:24][CH2:23][N:22]2[CH2:21][CH2:20][CH2:19]3)=[O:28])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 70389o-Amino-N-(2-chloro-3-pyridyl)benzamideHCID 19921765HCID 19921765, compound

Product 1

HCID 13933779HCID 13933779, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2-chloro-3-(2-aminobenzoyl)aminopyridine (15.0 g, 61.0 mmol), in 200 ml of anhydrous pyridine, pyrrolizidine-7a-carbonyl chloride hydrochloride (14.0 g, 80.5 mmol), prepared as described in Reference Example 3) was added at -20° C. The mixture was stirred for 17 hours at 10° C. and evaporated in vacuo to dryness. The remaining residue was partitioned between saturated sodium biscarbonate solution and chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to dryness. To the remaining residue, methanol was added. After stirring, the resulting crystals was obtained through filtration and washed with small amount of methanol to give 18.1 g (77.2%) of the desired compound.

Workup

  1. additionwas added at -20° C
  2. customevaporated in vacuo to dryness
  3. customThe remaining residue was partitioned between saturated sodium biscarbonate solution and chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to dryness
  7. additionTo the remaining residue, methanol was added
  8. stirringAfter stirring
  9. customthe resulting crystals was obtained through filtration
  10. washwashed with small amount of methanol

Sources & evidence

ORD record
ord-a66686fae88e47c0a7a456b2dd7ed851
Source dataset
uspto-grants-1988_03
Patent number
US04734411

Reaction notes

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