Hydroxybenzenesulfonic acid → HCID 21699705, compound

HRID 1597282Notes

Reaction equation

HRID 1597282 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([CH2:22][OH:23])[C:10]=2[CH2:9]1)=O)(C)(C)C.O.[C:25]1([S:31]([OH:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[C:25]1([S:31]([OH:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:25]1([S:31]([OH:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH:23][CH2:22][C:11]1[C:10]2[CH2:9][NH:8][CH2:17][CH2:16][C:15]=2[N:14]=[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=12

Participants

4

Reactant 2

HCID 15619088Hydroxybenzenesulfonic acidHCID 21699661HCID 21699661, compound

Product 1

HCID 21699705HCID 21699705, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

2-t-Butoxycarbonyl-10-hydroxymethyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine (202 mg, 0.643 mmol) was dissolved in methanol (1.3 ml), followed by adding thereto benzenesulfonic acid monohydrate (226.3 mg, 1.285 mmol), and the resulting mixture was heated under reflux at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure to obtain the desired compound (361.2 mg, quant.) as a brown substance.

Workup

  1. additionby adding
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1e7b2a8b7824120b9b3423fc2e403dd
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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