Hydrochloric Acid → Methyl suberanilate

HRID 418750

Reaction equation

HRID 418750 reaction equation
[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].Cl.[CH3:20]O>>[C:1]([O:18][CH3:20])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9543537Suberanilic Acid2×

Product 1

HCID 11265520Methyl suberanilate

Conditions

Temperature
50 °C

Procedure

Suberanilic acid (Compound 3, 249.3 g, 1.0 mole) and methanol (0.4-0.5 L) are combined and heated to 45-55° C. The pH is adjusted to ≦2 using hydrochloric acid, and the batch temperature is maintained at 45-55° C. until the reaction is complete. The reaction is quenched with deionized water (0.1-0.2 L). The batch is cooled to 25-30° C. and seeded to induce crystallization, and then cooled to 0-10° C. The batch is filtered, and the cake washed with a 50:50 (v/v) methanol/water solution (0.28-0.34 L) at 0-10° C. The wet cake is dried at a maximum of 46° C. under vacuum to yield methyl suberanilate.

Workup

  1. temperaturethe batch temperature is maintained at 45-55° C. until the reaction
  2. customThe reaction is quenched with deionized water (0.1-0.2 L)
  3. temperatureThe batch is cooled to 25-30° C.
  4. customcrystallization
  5. temperaturecooled to 0-10° C
  6. filtrationThe batch is filtered
  7. washthe cake washed with a 50:50 (v/v) methanol/water solution (0.28-0.34 L) at 0-10° C
  8. customThe wet cake is dried at a maximum of 46° C. under vacuum

Sources & evidence

ORD record
ord-5e2464984a5e4e54b7d3a09c88932a3c
Source dataset
uspto-grants-2012_01
Patent number
US08093295B2

Linked notes

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