O-Phenylenediamine → HCID 60001261, compound

HRID 1803832Notes

Reaction equation

HRID 1803832 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:9][C:10]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:11]=1[C:12](O)=O.[OH-].[Na+]>O>[CH3:9][C:10]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:11]=1[C:12]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 14798Sodium HydroxideHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 60001261HCID 60001261, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Benzene-1,2-diamine (2.60 g, 25 mmol) and 2-methyl-5-nitrobenzoic acid (5.0 g, 27.6 mmol) were suspended in polyphosphoric acid (30 ml, 11 vol) and heated to 140° C. overnight. Once the reaction had gone to completion (monitored by LCMS), the crude green mixture was dissolved in water, basified with NaOH (pH=14) and extracted into EtOAc (×2). The organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 7 (4.70 g, 74%) as an orange/brown solid: 1H NMR (C2D6SO) δ 13.20 (s, 1H), 8.80 (app d, 1H), 8.84 (dd, 1H), 7.89-7.87 (m, 2H), 7.74 (d, 1H), 7.40-7.45 (m 2H), 2.90 (s, 3H); MS (ES, positive mode): 254 [M++1].

Workup

  1. extractionextracted into EtOAc (×2)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-805a0ea99fd742c592e5ce59944826c4
Source dataset
uspto-grants-2013_01
Patent number
US08354397B2

Reaction notes

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