O-Phenylenediamine → HCID 60001261, compound

HRID 1618941Notes

Reaction equation

HRID 1618941 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 (x 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 (x 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-adccf0a15a7348c5a3b2ae4f7a5afb35
Source dataset
uspto-grants-2014_07
Patent number
US08772275B2

Reaction notes

Loading…