8-Amino-2-naphthalenol → HCID 54062299, compound

HRID 972437Notes

Reaction equation

HRID 972437 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.[CH2:13]([S:29](Cl)(=[O:31])=[O:30])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>N1C=CC=CC=1>[CH2:13]([S:29]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2)(=[O:31])=[O:30])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 83588-Amino-2-naphthalenolHCID 969231-Hexadecanesulfonyl chloride

Product 1

HCID 54062299HCID 54062299, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 51.4 g (0.33 mole) 8-amino-2-naphthol in 500 ml pyridine was cooled to 0° and treated with 108.0 g (0.33 mole) hexadecanesulfonyl chloride. The mixture was stirred briefly at 0° C. and overnight at room temperature, then poured into ice water containing 500 ml concentrated hydrochloric acid. The solid was collected, washed, dried, and recrystallized from benzene to give 100 g of product, m.p. 103.5°-107° C.

Workup

  1. customThe solid was collected
  2. washwashed
  3. customdried
  4. customrecrystallized from benzene

Sources & evidence

ORD record
ord-69e28eb2c4e84d0ca7f2cebf0f2e6853
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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