Hydrochloric Acid → HCID 67314095, compound

HRID 1012049Notes

Reaction equation

HRID 1012049 reaction equation
CON(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[C:14]1(Br)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C([Li])CCC.Cl>C1COCC1>[C:14]1([C:27]2([C:4](=[O:12])[C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[NH2:7])[CH:26]=[CH:25][CH:30]=[CH:29][CH2:28]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 70011-BromonaphthaleneHCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 178418244HCID 178418244, compound

Product 1

HCID 67314095HCID 67314095, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The reaction of the above-mentioned scheme 2 was performed specifically as follows. That is, first, anthranilic acid N-methoxy-N-methylamide (5-1) (2.00 g, 11.1 mmol) and 1-naphthyl bromide (5-2) (2.29 g, 11.1 mmol) were dissolved in 60 mL of dehydrated THF. Next, this solution was cooled to −78° C., and while this temperature was maintained, an n-butyllithium hexane solution (13.8 mL, 1.6 M, and 22.2 mmol) was dropped thereinto over 20 minutes with stirring. After dropping, 20 mL of 1N hydrochloric acid was added thereto and extraction was performed with 150 mL of ethyl acetate. This was washed with 100 mL of water twice and subsequently was washed with 50 mL of saturated saline. The organic solvent was removed therefrom and this was then purified by column chromatography using chloroform as a developing solvent. Thus 1′-naphthyl-2-aminobenzophenone (5-3) was obtained. The yield amount was 500 mg, and the yield was 18%. The instrumental analysis data of this 1′-naphthyl-2-aminobenzophenone (5-3) is indicated below.

Workup

  1. customThe reaction of the above-mentioned scheme 2
  2. temperaturewhile this temperature was maintained
  3. extractionextraction
  4. washThis was washed with 100 mL of water twice
  5. washsubsequently was washed with 50 mL of saturated saline
  6. customThe organic solvent was removed
  7. customthis was then purified by column chromatography

Sources & evidence

ORD record
ord-c69f15038cab4043832d0458535b5c09
Source dataset
uspto-grants-2011_07
Patent number
US07977486B2

Reaction notes

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