4-Chloro-1,2-diaminobenzene → N-(2-amino-4-chlorophenyl)-6-chloronicotinamide

HRID 1695048Notes

Reaction equation

HRID 1695048 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[C:43]([NH2:48])[CH:42]=1>[Cl-].[Na+].O.CN(C=O)C>[NH2:48][C:43]1[CH:42]=[C:41]([Cl:40])[CH:46]=[CH:45][C:44]=1[NH:47][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

8

Reactant 5

HCID 72634-Chloro-1,2-diaminobenzeneHCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 22668939N-(2-amino-4-chlorophenyl)-6-chloronicotinamideYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-Chloronicotinic acid (157.5 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 4-chloro-o-phenylenediamine (171 mg, 1.2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine and extracted with 200 ml of ethyl acetate. The ethyl acetate was removed under vacuum. To the residue was added 5 ml of absolute ethanol. The solids were collected by vacuum filtration, washed with absolute ethanol and dried under vacuum to give the title compound (135 mg, 48% yield) as a brown solid. LC-MS (m/z) 282 (M+1).

Workup

  1. additionwere added
  2. extractionextracted with 200 ml of ethyl acetate
  3. customThe ethyl acetate was removed under vacuum
  4. additionTo the residue was added 5 ml of absolute ethanol
  5. filtrationThe solids were collected by vacuum filtration
  6. washwashed with absolute ethanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-962de30396b64265b5287ca0bd306bc4
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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