Hydrochloric Acid → HCID 19106989, compound

HRID 1460600Notes

Reaction equation

HRID 1460600 reaction equation
C[CH:2]1[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])(C(O)=O)[C:6](=[O:19])[CH2:5][CH2:4][N:3]1C(=O)C1C=CC=CC=1.[ClH:28]>>[ClH:28].[Br:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH:7]1[C:6](=[O:19])[CH2:5][CH2:4][NH:3][CH2:2]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19107064HCID 19107064, compound

Product 1

HCID 19106989HCID 19106989, compoundYield 77%

Procedure

The ketoester (18.5 g, 0.043 mol) from Example 101 was suspended in 6N hydrochloric acid and refluxed for 18 hours. The reaction was cooled and the benzoic acid was filtered and washed with water. The filtrate was washed with ether (2×75 ml) and the aqueous layer was concentrated under reduced pressure. The crude residue was crystallized from ethanol and ethyl ether to produce the title compound (10.1 g, 77%) as a white solid, mp 198°-200° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe benzoic acid was filtered
  4. washwashed with water
  5. washThe filtrate was washed with ether (2×75 ml)
  6. concentrationthe aqueous layer was concentrated under reduced pressure
  7. customThe crude residue was crystallized from ethanol and ethyl ether

Sources & evidence

ORD record
ord-995a19eebdd74d539f6065730b96e343
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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