Methanol → HCID 67520240, compound

HRID 2115810Notes

Reaction equation

HRID 2115810 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21]([C:25]([OH:27])=[O:26])=[CH:20][CH:19]=[C:18]2[N:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO>ClCCl.CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21]([C:25]([O:27][CH3:1])=[O:26])=[CH:20][CH:19]=[C:18]2[N:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 67520549HCID 67520549, compound

Product 1

HCID 67520240HCID 67520240, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (2.60 g, 1.79 mL, 20.5 mmol) was added dropwise to a solution of 6-(benzyloxy)-4-(dibenzylamino)-1-naphthoic acid (3.236 g, 6.834 mmol) in dichloromethane (70 mL) and DMF (1 drop). The mixture stirred at RT for 1 h and was concentrated to afford a yellow solid. CH2Cl2 (60 mL) was added followed by the dropwise addition of MeOH(10 mL), and the mixture stirred at RT for 45 min. The mixture was concentrated to afford methyl 6-(benzyloxy)-4-(dibenzylamino)-1-naphthoate as a light brown solid. MS (ESI, pos. ion) m/z: 488.2 (M+H). Mass Calc'd for C33H29NO3: 487.

Workup

  1. concentrationwas concentrated
  2. customto afford a yellow solid
  3. stirringthe mixture stirred at RT for 45 min
  4. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-c430075ce2ef4fb9a1e68ce3f7465204
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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