Hydrochloric Acid → HCID 19106989, compound

HRID 1197547Notes

Reaction equation

HRID 1197547 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-066e77101045449f9d24b04b663e5621
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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