Acetic acid, 2,2-dimethoxy-, methyl ester → HCID 67338446, compound

HRID 1671466Notes

Reaction equation

HRID 1671466 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:15][O:16][CH:17]([O:22]C)[C:18](OC)=O>N>[CH3:15][O:16][C:17]([CH:18]1[NH:1][C:2]2[N:3]=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)=[O:22]

Participants

4

Reactant 2

HCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 147619283-Benzylpyridin-2-amine

Product 1

HCID 67338446HCID 67338446, compoundYield 337%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 2-amino-3-benzylpyridine (18.3 g, 99.4 mmol; crude) and methyl 2,2-dimethoxyacetate (22 g, 21.6 mmol, 1.9 eq.) in a 250 ml round-bottomed flask was treated at room temperature with concentrated, sulphuric acid (50 ml) by quick addition while stirring. A vigorous exothermic reaction took place. After stirring for 30 minutes the dark mixture was poured on ice water (1000 ml). Concentrated ammonia (25% aq.; 250 ml) was added to basify the mixture. Extraction with dichloromethane (2×150 ml). The combined organic layers were dried with Na2SO4. Evaporation under vacuum gave 10,11-dihydro-5H-benzo[e]pyrido[2,3-b]azepine-10-carboxylic acid methyl ester as a yellow foam (18.5 g, 72.8 mmol) in 73% yield. An analytically pure sample can be obtained by chromatography on silica gel. Rf=0.3 (EtOAc/n-heptane=1:1).

Workup

  1. additionwas treated at room temperature
  2. concentrationwith concentrated
  3. additionsulphuric acid (50 ml) by quick addition
  4. customA vigorous exothermic reaction
  5. stirringAfter stirring for 30 minutes the dark mixture
  6. additionwas poured on ice water (1000 ml)
  7. extractionExtraction with dichloromethane (2×150 ml)
  8. dry with materialThe combined organic layers were dried with Na2SO4
  9. customEvaporation under vacuum

Sources & evidence

ORD record
ord-49783eaa212d46b48b8ee8b73bbe28a0
Source dataset
uspto-grants-2011_08
Patent number
US07994314B2

Reaction notes

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