Hydrochloric Acid → HCID 136380425, compound

HRID 1792833Notes

Reaction equation

HRID 1792833 reaction equation
[N+:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([O-])=O.Cl.NC1C=CC=CC=1.[N:19]([O-:21])=[O:20].[Na+].[C:23]1([OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-:30].[Na+]>O>[N+:19]([C:6]1[C:5]([N:4]=[N:1][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[OH:29])=[C:10]([OH:30])[CH:9]=[CH:8][CH:7]=1)([O-:21])=[O:20]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 996PhenolHCID 6115AnilineHCID 14798Sodium HydroxideHCID 61191N-NitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 136380425HCID 136380425, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Nitro aniline (138.13 g) was mixed with 500 mL of concentrated HCl and stirred for several min. When all the aniline was dissolved, the solution was cooled down to room temperature and diluted with water (300 mL), and then a solution of NaNO2 (69 g) in 250 mL of water was dropwise added at 0° C. The solution became a clear and yellowish solution. The diazonium salt solution was added slowly to a solution of phenol (128.5 g) in water (800 mL) containing 80 g of NaOH at 0° C. When the addition was complete, the reaction mixture was stand for several hours, a black precipitate was formed and filtered. The solid was dissolved in ethyl acetate, washed with brine, dried over anhydrous Na2SO4. The solution was concentrated to give 133.5 g of nitroazophenol product as light yellow solid. The mother liquor was concentrated again to give another 65 g of the nitroazophenol product. 1H-NMR (400 MHz, CDCl3): δ 10.98 (s, 1H), 8.20–7.05 (m, 7H).

Workup

  1. additionWhen the addition
  2. customfor several hours
  3. customa black precipitate was formed
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-ea5003e1ea4245e69a25cbcadf491b4f
Source dataset
uspto-grants-2006_07
Patent number
US07078421B2

Reaction notes

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