Реакция #91033

Уравнение реакции

HCl

methyl 4-chloro-3-methoxy-5-nitrobenzoate

Methyl 4-chloro-3-methoxy-5-nitrobenzoate

→

methyl 3-amino-4-chloro-5-methoxybenzoate

Выход 103.9%

Растворители

EtOH

water

Условия реакции

Обработка

1. 1
   Другоеdegassed with nitrogen for 20 min
2. 2
   workup.ADDITIONCelite (1 g) was added
3. 3
   workup.STIRRINGthe suspension stirred for 10 min
4. 4
   Фильтрацияthen filtered through a celite pad
5. 5
   ДругоеThe solvent was removed in vacuo
6. 6
   Другоеthe residue was partitioned between EtOAc (15 mL) and water (15 mL)
7. 7
   ДругоеThe phases were separated
8. 8
   Промывкаthe organic solution was washed with brine (2×15 mL)
9. 9
   ДругоеThe solvent was removed in vacuo

Методика

A suspension of methyl 4-chloro-3-methoxy-5-nitrobenzoate (3) (900 mg, 3.66 mmol) and iron powder (614 mg, 11.0 mmol) in a mixture of EtOH (15 mL) and water (15 mL) was heated to 70° C. and degassed with nitrogen for 20 min. Conc. HCl (44.5 μL, 1.47 mmol) was added and the reaction mixture was stirred at 70° C. for 3 h. Celite (1 g) was added and the suspension stirred for 10 min then filtered through a celite pad. The solvent was removed in vacuo and the residue was partitioned between EtOAc (15 mL) and water (15 mL). The phases were separated and the organic solution was washed with brine (2×15 mL). The solvent was removed in vacuo to afford methyl 3-amino-4-chloro-5-methoxybenzoate (0.82 g, 100% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ: 7.10 (1H, d), 6.78 (1H, d), 5.68 (2H, s), 3.81 (6H, m).

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