Hydrochloric Acid → Methyl 4-amino-2-ethoxy-5-nitrobenzoate

HRID 1088344Notes

Reaction equation

HRID 1088344 reaction equation
Cl.C([NH:5][C:6]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([O:19][CH2:20][CH3:21])[CH:7]=1)(=O)C>>[NH2:5][C:6]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([O:19][CH2:20][CH3:21])[CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 150967504-(Acetylamino)-2-ethoxy-5-nitrobenzoic Acid Methyl Ester

Product 1

HCID 15096751Methyl 4-amino-2-ethoxy-5-nitrobenzoateYield 42.2%

Procedure

To 100 parts of a hydrochloric acid solution 6N were added 5.65 parts of methyl 4-(acetylamino)-2-ethoxy-5-nitrobenzoate and the whole was stirred and refluxed for 30 minutes. After cooling, the precipitated product was filtered off and crystallized from 80 parts of 2-propanol at 0° C. The product was filtered off and dried, yielding 1.9 parts (42.2%) of methyl 4-amino-2-ethoxy-5-nitrobenzoate; mp. 210° C.;(intermediate 33).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe precipitated product was filtered off
  4. customcrystallized from 80 parts of 2-propanol at 0° C
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-f8acea30b04b4ee0872b5ff8bf811b90
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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