Hydrochloric Acid → ethyl 7-iodo-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate

HRID 2373357Notes

Reaction equation

HRID 2373357 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:11]=1[C:12]([O:14]C)=O)=[O:8])[CH3:2].CC([O-])(C)C.[K+].O.Cl>C1COCC1>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][C:7](=[O:8])[NH:9][C:10]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:11]=2[C:12]1=[O:14])=[O:21])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 66935113Methyl 2-(4-ethoxy-4-oxobutanamido)-5-iodobenzoate

Product 1

HCID 66934628ethyl 7-iodo-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 2-(4-ethoxy-4-oxobutanamido)-5-iodobenzoate (ii-a) (22.0 g, 54 mmol) in 125 mL of THF was added a 1 M solution of KOt-Bu in THF (119 mL, 119 mmol). The reaction was complete after 2.5 h at 22° C. H2O (250 mL) and 1N HCl (60 mL) were added to the solution, and the resulting precipitate was filtered, washed with 2×50 mL Et2O, and dried in vacuo to give iii-a (16.1 g, 83%) as a whitish/gray solid as a mixture of ethyl and methyl esters: MS m/z═374 (M+H) and 360 (M+H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with 2×50 mL Et2O
  3. customdried in vacuo
  4. customto give iii-a (16.1 g, 83%) as a whitish/gray solid

Sources & evidence

ORD record
ord-c5bc26bcefbf47f888368af474e452a1
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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