3,4-Diamino-5-methylbenzoic acid → HCID 136106278, compound

HRID 470358Notes

Reaction equation

HRID 470358 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([O:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][C:3]=1[CH:4]=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:29])[C:27]=1[NH2:28])[C:22]([OH:24])=[O:23]>CC(N(C)C)=O>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([O:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][C:3]=1[C:4]1[NH:18][C:19]2[CH:20]=[C:21]([C:22]([OH:24])=[O:23])[CH:25]=[C:26]([CH3:29])[C:27]=2[N:28]=1

Participants

4

Reactant 2

HCID 534395813,4-Diamino-5-methylbenzoic acidHCID 59784178HCID 59784178, compound

Product 1

HCID 136106278HCID 136106278, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

To mixture of 2-hydroxy-5-(2-methoxy-pyridin-3-yl)-benzaldehyde (144 mg, 0.4 mmol) and 3,4-diamino-5-methyl-benzoic acid (82 mg, 0.5 mol) was added DMA (0.8 mL) and the resulting solution was stirred at 0° C. for 0.5 h, and at the room temperature for 2.5 h. After it was heated open to the air at 110° C. for 15 h, the reaction mixture was concentrated under reduced pressure and the residual crude was used for the next step reaction without purification. ESI-MS m/z 376.3 (MH+).

Workup

  1. waitat the room temperature for 2.5 h
  2. temperatureAfter it was heated open to the air at 110° C. for 15 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residual crude was used for the next step reaction without purification

Sources & evidence

ORD record
ord-9431a2ef900348f5bff640f214d21fd7
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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