Methanol → HCID 67520240, compound

HRID 1925306Notes

Reaction equation

HRID 1925306 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-16241a4af0884ec8815d846901e59579
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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