Dichloromethane → HCID 70983733, compound

HRID 338883Notes

Reaction equation

HRID 338883 reaction equation
[NH2:1][C:2]1[C:3]([CH:11]2[CH2:13][CH2:12]2)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH:14](=O)/[CH:15]=[CH:16]/[CH3:17].[OH-].[Na+].C(Cl)Cl>Cl>[CH:11]1([C:3]2[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[C:10]3[C:2]=2[N:1]=[C:16]([CH3:17])[CH:15]=[CH:14]3)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 447466CrotonaldehydeHCID 86707430HCID 86707430, compound

Product 1

HCID 70983733HCID 70983733, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-amino-2-cyclopropylbenzoic acid (0.507 g, 2.86 mmol) in 6 N HCl (8 mL) was added (E)-but-2-enal (0.47 mL, 5.72 mmol) dropwise at reflux. The reaction mixture was stirred at reflux for 2 hours. After cooling to ambient temperature, the reaction mixture was basified with sodium hydroxide to about pH 12 and DCM (20 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to about pH 3-4. The aqueous layer was then extracted with 3:1 CHCl3/IPA (2×30 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure to give 8-cyclopropyl-2-methylquinoline-7-carboxylic acid (0.18 g, 27.7%) as a solid.

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 2 hours
  3. additionwas added
  4. customThe aqueous layer was separated
  5. extractionThe aqueous layer was then extracted with 3:1 CHCl3/IPA (2×30 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6616a93cd307471b8229765e088914ed
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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