O-Phenylenediamine → HCID 21883720, compound

HRID 722320Notes

Reaction equation

HRID 722320 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=O)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=2[CH:20]=1.[C:23]1([NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29]>[N+](C1C=CC=CC=1)([O-])=O>[NH:29]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:30]=[C:21]1[C:4]1[C:5]2[O:10][CH:9]([C:11]([F:12])([F:14])[F:13])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=2[CH:20]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 21883599HCID 21883599, compound

Product 1

HCID 21883720HCID 21883720, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of the aldehyde (Example 76, Step 3) (0.33 g, 0.99 mmol) and 1,2-phenylenediamine (0.11 g, 1.02 mmol) in nitrobenzene (20 mL) was heated to 150° C. for 1.8 hours. The reaction mixture was extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo and purified by flash chromatography over silica gel (with 1:9 ethyl acetate/hexane as eluant) to give the ester as a brown solid (0.18 g, 43%) which was used in the next step without further purification.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography over silica gel (with 1:9 ethyl acetate/hexane as eluant)

Sources & evidence

ORD record
ord-c94cef33dfc1422d82b19bd1e7dcb7ad
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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