Trimethyl orthoformate → HCID 118323954, compound

HRID 1778269Notes

Reaction equation

HRID 1778269 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[CH3:14][C:15]1([CH3:23])[O:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[O:16]1.[CH:24](OC)(OC)OC>>[CH3:14][C:15]1([CH3:23])[O:20][C:19](=[O:21])[C:18](=[CH:24][NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[O:12][CH3:13])[C:17](=[O:22])[O:16]1

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 602411Methyl 4-amino-3-methoxybenzoate

Product 1

HCID 118323954HCID 118323954, compound

Conditions

Temperature
100 °C

Procedure

Into a 250-mL round-bottom flask, was placed methyl 4-amino-3-methoxybenzoate (10 g, 55.19 mmol, 1.00 equip), 2,2-dimethyl-1,3-dioxane-4,6-dione (9.5 g, 65.91 mmol, 1.20 equip), (CH3O)3CH (100 mL). The resulting solution was stirred overnight at 100° C. The reaction mixture was cooled with a water/ice bath. The solids were collected by filtration to yield methyl 4-[[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino]-3-methoxybenzoate as a light yellow solid. LCMS (ES, m/z) 336 [M+H]+

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. temperatureThe reaction mixture was cooled with a water/ice bath
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-96880ea7a5704ab5bdaf2aee3234f9f1
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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