Hydrochloric Acid → HCID 22667768, compound

HRID 1007131Notes

Reaction equation

HRID 1007131 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]([CH:22]=2)[C:18]([O:20][CH3:21])=[O:19])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 15049977Methyl 5-Amino-2-methylbenzoate

Product 1

HCID 22667768HCID 22667768, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyanobenzoyl chloride (4.50 g) was added to a stirred suspension of methyl 5-amino-2-methylbenzoate (J. Med. Chem., 1991, 34, 2176-2186; 3 g), triethylamine (2.54 ml) and methylene chloride (100 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The mixture was acidified by the addition of 1N aqueous hydrochloric acid solution and the mixture was stirred at ambient temperature for 30 minutes. The resultant solid was isolated and dried under vacuum at 40° C. to give methyl 5-(4-cyanobenzamido)-2-methylbenzoate (5.32 g); NMR Spectrum: (DMSOd6) 2.47 (s, 3H), 3.83 (s, 3H), 7.31 (d, 1H), 7.88 (d, 1H), 8.0 (d, 2H), 8.1 (d, 2H), 8.27 (s,1H), 10.57 (s, 1H); Mass Spectrum: M+H+ 295.

Workup

  1. customThe resultant solid was isolated
  2. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-933645b372044433848c857d04be0543
Source dataset
uspto-grants-2004_09
Patent number
US06794380B2

Reaction notes

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