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Chemical Structure| 38487-91-1 Chemical Structure| 38487-91-1

Structure of 2-Amino-4-methoxybenzamide
CAS No.: 38487-91-1

Chemical Structure| 38487-91-1

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Product Details of [ 38487-91-1 ]

CAS No. :38487-91-1
Formula : C8H10N2O2
M.W : 166.18
SMILES Code : O=C(N)C1=CC=C(OC)C=C1N
MDL No. :MFCD10566483

Safety of [ 38487-91-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 38487-91-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 38487-91-1 ]

[ 38487-91-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1039948-89-4 ]
  • [ 38487-91-1 ]
  • [ 1246250-42-9 ]
YieldReaction ConditionsOperation in experiment
58% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 115℃; for 16.0h; To a solution of 2-amino-4-methoxy-benzamide (1.00 g, 6.01 mmol) and <strong>[1039948-89-4]4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde</strong> (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was stirred at 115 C. for 16 hours, and cooled to room temperature. Solvent was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 hour, filtered, and dried under vacuum, to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-7-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.20 g (58%).
58% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 115℃; for 16.0h; To a solution of 2-amino-4-methoxy-benzamide (1.00 g, 6.01 mmol) and <strong>[1039948-89-4]4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde</strong> (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was stirred at 115 C. for 16 hours, and cooled to room temperature. Solvent was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 hour, filtered, and dried under vacuum, to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-7-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.20 g (58%).
  • 2
  • [ 52351-75-4 ]
  • [ 38487-91-1 ]
YieldReaction ConditionsOperation in experiment
72% With ammonium hydroxide; dihydrogen peroxide; In dimethyl sulfoxide; at 20 - 30℃; for 4h;Sealed tube; General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).
 

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