3-ethoxy-4-methylaniline → HCID 21908691, compound

HRID 1505369Notes

Reaction equation

HRID 1505369 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[CH3:11])N)[CH3:2].N([O-])=[O:13].[Na+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:8]=[CH:9][C:10]=1[CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 2963233-ethoxy-4-methylaniline2×HCID 23668193Sodium Nitrite

Product 1

HCID 21908691HCID 21908691, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of 3-(ethyloxy)-4-methylaniline (Intermediate 89, 300 mg) in a mixture of water/concentrated sulfuric acid 98% (20 mL/7 mL) under argon was cooled at 0° C. A solution of sodium nitrite (151 mg, 2.182 mmol) in 4 mL of water was slowly added. The reaction mixture was stirred at 0° C. for 1 hour 30. The reaction mixture was then slowly added to a solution of water/concentrated sulfuric acid (18 mL/5 mL) pre-heated at 90° C. The reaction mixture was stirred at 90° C. for 1 hour 15. After cooling down, the reaction mixture was extracted with ethyl ether (4 times). The gathered organic phases were dried over sodium sulphate, filtered and concentrated under vacuum to afford the compound (276 mg).

Workup

  1. temperaturepre-heated at 90° C
  2. stirringThe reaction mixture was stirred at 90° C. for 1 hour 15
  3. temperatureAfter cooling down
  4. extractionthe reaction mixture was extracted with ethyl ether (4 times)
  5. dry with materialThe gathered organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-538f3fc5e626482ea4daf2e048a98e4e
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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