3,5-Diamino-2-methylbenzoic acid → HCID 136387988, compound

HRID 1360723Notes

Reaction equation

HRID 1360723 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[CH3:13][C:14]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([CH3:23])[C:15]=1[CH:16]=O>CS(C)=O.O>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[N:12]=[C:16]([C:15]3[C:14]([CH3:13])=[CH:21][C:20]([OH:22])=[CH:19][C:18]=3[CH3:23])[NH:1][C:2]=2[CH:3]=1)=[O:6]

Participants

5

Reactant 2

HCID 1355243,5-Diamino-2-methylbenzoic acidHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 136387988HCID 136387988, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

3.65 g of methyl 3,4-diaminobenzoate and 3.3 g of 2,6-dimethyl-4-hydroxybenzaldehyde were stirred in 25 ml of DMSO at room temperature. A solution of 170 mg of FeCl3 in 5 ml of DMSO was added by pipet and the reaction was stirred at the same temperature for 5 days. The reaction was then diluted with water and the resulting precipitates were collected by filtration. The filter cake was washed with water and heptane, and dried by air in the suction funnel to afford the title compound. LCMS retention T=1.01 min. (M+H)+=297.01, Method 10.

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. washThe filter cake was washed with water and heptane
  4. customdried by air in the suction funnel

Sources & evidence

ORD record
ord-094da6ea81f24883b9c9356aaac99b2d
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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