1-Naphthol → HCID 19959520, compound

HRID 54605Notes

Reaction equation

HRID 54605 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C1C=CC2C(=CC=CC=2O)C=1.[Cl:23]Cl.[CH2:25]([N:27](CC)[CH2:28][CH3:29])[CH3:26].N1CCCC1>C1(C)C=CC=CC=1>[Cl:23][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:27]2[CH2:28][CH2:29][CH2:26][CH2:25]2)=[CH:3][C:2]=1[OH:11]

Participants

7

Reactant 5

HCID 70051-NaphtholHCID 8471TriethylamineHCID 86632-NaphtholHCID 24526ChlorineHCID 31268Pyrrolidine

Product 1

HCID 19959520HCID 19959520, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-Naphthol (14.43 g; 0.100 mol) was dissolved in toluene (200 ml) by warming. The pale brown solution was cooled and vigorously stirred until the naphthol began to precipitate and chlorine (15.22 g;0.21 mol) was then passed through the solution at approximately 2.5-3.0 g/min followed immediately by nitrogen gas. The resulting amber solution was treated firstly with triethylamine (12.12 g;0.12 mol) in one portion and then with a solution of pyrrolidine (7.10;0.10 mol), in toluene (100 ml), dropwise over 1.5 hours keeping the temperature at 15°-20° C. The resulting brown mixture was filtered to remove triethylamine hydrochloride as a white amorphous solid. The toluene filtrate was washed with water, dried and evaporated to give 1-chloro-4-pyrrolidino-2-naphthol as a brown viscous oil (25.87 g). Purification by chromatography over silica (eluent: toluene) gave the product as a red-brown oil (3.825 g;15%). ##STR27## (b) 4-Pyrrolidino-2-naphthol

Workup

  1. temperatureby warming
  2. temperatureThe pale brown solution was cooled
  3. customto precipitate
  4. customat 15°-20° C
  5. filtrationThe resulting brown mixture was filtered
  6. customto remove triethylamine hydrochloride as a white amorphous solid
  7. washThe toluene filtrate was washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-419c768776844f5cb86fd5b3f3c076ef
Source dataset
uspto-grants-1997_04
Patent number
US05623005

Reaction notes

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