Sulfuric Acid → Methyl 2-acetamido-3-(cyclopropylmethoxy)-4-methoxybenzoate

HRID 1095785Notes

Reaction equation

HRID 1095785 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:16]([O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)=[C:15]([O:22][CH3:23])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([NH:6][C:7]1[C:16]([O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)=[C:15]([O:22][CH3:23])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 53441652Methyl 2-amino-3-(cyclopropylmethoxy)-4-methoxybenzoate

Product 1

HCID 53441632Methyl 2-acetamido-3-(cyclopropylmethoxy)-4-methoxybenzoateYield 65.4%

Conditions

Temperature
30 °C

Procedure

Sulfuric acid (1 mL) was added dropwise to a solution of methyl 2-amino-3-(cyclopropylmethoxy)-4-methoxybenzoate (98%, 187 g, 0.73 mol) and acetic anhydride (372 g, 3.65 mol). The reaction was warmed at 30° C. overnight, quenched with water/ice (1.5 L), and then stirred vigorously for 30 min. The resulting solids were collected by filtration and dried in an oven to give 140 g of methyl 2-acetamido-3-(cyclopropylmethoxy)-4-methoxybenzoate as a white solid. MS (ESI): 293.9.

Workup

  1. customquenched with water/ice (1.5 L)
  2. filtrationThe resulting solids were collected by filtration
  3. customdried in an oven

Sources & evidence

ORD record
ord-f6231d48438c48e9bcac8df833a66000
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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