Benzamide, 3-amino-4-chloro- → HCID 59479517, compound

HRID 1515500Notes

Reaction equation

HRID 1515500 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH2:7])=[O:6].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].O.[C:26]([OH:30])(=[O:29])[CH:27]=O>C(Cl)Cl.CN(C=O)C>[C:5]([C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([NH:1][CH:27]([C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:26]([OH:30])=[O:29])[CH:3]=1)(=[O:6])[NH2:7]

Participants

6

Reactant 3

HCID 88200Benzamide, 3-amino-4-chloro-HCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 59479517HCID 59479517, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-amino-4-chlorobenzamide (170 mg, 1.0 mmol), 3,4-dimethoxyphenylboronic acid (182 mg, 1.0 mmol) and glyoxylic acid monohydrate (92 mg, 1.0 mmol) in methylene chloride (4.0 mL) and DMF (0.3 mL) was heated at 65° C. for 3.0 h and then stirred at rt for 18 h. The precipitate formed was collected by filtration and washed with methylene chloride to give 3A (200 mg, 57% yield) after drying. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.80 (s, 3H) 3.81 (s, 3H) 5.17 (s, 1 H) 6.92 (d, J=8.35 Hz, 1H) 7.04 (s, 1H) 7.04-7.11 (m, 3H) 7.33 (d, J=7.91 Hz, 1 H); LC-MS 365 (M+H).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with methylene chloride

Sources & evidence

ORD record
ord-ede204400a934baf82962eab4a5492d5
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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