Hydrochloric Acid → HCID 22120164, compound

HRID 1274099Notes

Reaction equation

HRID 1274099 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[CH:5]=[CH:4][C:3]1=2.Br[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22](C(O)=O)[CH:21]=[CH:20]2.CN1C[CH2:35][O:34][CH2:33]C1.Cl.[O:38]1CCOCC1>>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:22]3[CH:23]=[C:24]4[C:19](=[CH:20][CH:21]=3)[C:18]([C:33]([O:34][CH3:35])=[O:38])=[CH:17][CH:26]=[CH:25]4)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 312751,4-DioxaneHCID 45498526-Bromo-2-naphthalenecarboxylic acidHCID 114697605,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Product 1

HCID 22120164HCID 22120164, compoundYield 10%

Procedure

4.04 g (19.9 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine, 5 g (19.9 mmol) of 6-bromo-2-naphthoic acid, 3.3 ml (30 mmol) of N-methyl-morpholine, 2.9 g (19.9 mmol) of Cu2O and 60 ml of dioxane were introduced in succession into a round-bottomed flask. The mixture was heated at reflux for 24 hours, the reaction medium was poured into 60 ml of 5N hydrochloric acid, and the precipitate was filtered off, washed with water and dried. The solid was purified by chromatography on a silica column eluted with ethyl acetate and, after evaporation of the solvents, 1.2 g of the expected acid was recovered, which was converted into the methyl ester by reacting same with 50 ml of methyl alcohol in the presence of 100 μl of concentrated sulfuric acid. 720 mg (10%) of methyl 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamino)naphthoate were obtained, in the form of a chestnut brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customThe solid was purified by chromatography on a silica column
  7. washeluted with ethyl acetate
  8. customafter evaporation of the solvents, 1.2 g of the expected acid
  9. customwas recovered

Sources & evidence

ORD record
ord-30b3d6cbd440472fb77980817583ded8
Source dataset
uspto-grants-2000_12
Patent number
US06156750

Reaction notes

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