Sulfuric Acid → 7-amino-4-chloromethylcoumarin

HRID 1901232Notes

Reaction equation

HRID 1901232 reaction equation
C([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([CH2:18][Cl:19])=[CH:12][C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1)(OCC)=O.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[NH2:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([CH2:18][Cl:19])=[CH:12][C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 2434815Ethyl (4-ChloroMethyl)couMarin-7-carbaMate

Product 1

HCID 27625987-amino-4-chloromethylcoumarinYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 7-carbethoxyamino-4-chloromethylcoumarin (2.81 g, 0.01 mole), concentrated sulfuric acid (10 mL) and glacial acetic acid (10 mL) is heated at 130° C. in an oil bath for 1 hour. On cooling, a yellow precipitate is deposited. The mixture is poured into 200 mL of ice-water and left overnight. The resulting solution is made slightly basic (pH 8) with dilute NaOH solution and is then cooled by the addition of ice chips. The yellow precipitate is filtered, washed with water and dried. The product is recrystallized from chloroform to give yellow needles. Yield: 79%.

Workup

  1. temperatureOn cooling
  2. temperatureis then cooled by the addition of ice chips
  3. filtrationThe yellow precipitate is filtered
  4. washwashed with water
  5. customdried
  6. customThe product is recrystallized from chloroform
  7. customto give yellow needles

Sources & evidence

ORD record
ord-e16c89fbd7a34f76af8cf11e598dfeec
Source dataset
uspto-grants-1996_11
Patent number
US05576424

Reaction notes

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