Anthranilamide → HCID 13521076, compound

HRID 1354978Notes

Reaction equation

HRID 1354978 reaction equation
C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[NH2:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([NH2:40])=[O:39].C([O-])([O-])=O.[K+].[K+].Cl[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH3:58]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([NH2:40])=[O:39].[NH2:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([NH:40][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH3:58])=[O:39]

Participants

7

Reactant 4

HCID 6942AnthranilamideHCID 72382-ChlorotolueneHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 2

HCID 7208552-amino-N-(2-methylphenyl)benzamideYield 10%HCID 13521076HCID 13521076, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (19.0 mg, 0.04 mmol), 2-aminobenzamide (170 mg, 1.25 mmol) and K2CO3 (173 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. 2-Chlorotoluene (60 μL, 0.5 mmol) and tbutanol (1 mL) were added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 110° C. The reaction mixture was stirred for 17 h, allowed to cool down to room temperature and filtered through celite with ethyl acetate. The filtrate was concentrated under reduced pressure. Chromatography on silica gel column with 4:1 hexane:ethyl acetate gave 98 mg (87%) of 2-(2-methylphenylamino)benzamide as a white solid and 11 mg (10%) of 2-amino-N-(2-methylphenyl)benzamide as a white solid.

Workup

  1. additionAn oven-dried resealable schlenk tube containing a stir bar
  2. customThe tube was capped with a rubber septum
  3. customevacuated
  4. customscrew cap
  5. customThe schlenk tube was sealed
  6. customput into a pre-heated oil bath at 110° C
  7. filtrationfiltered through celite with ethyl acetate
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a6ae417b06e74d4aba38c4df9f724ff2
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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