Sodium Carbonate → 3-(2-Aminonaphthalen-1-yl)benzoic acid

HRID 1526158Notes

Reaction equation

HRID 1526158 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.O.[Na].[Na].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.Br[C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[NH2:42].[C:43]([C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1)([OH:45])=[O:44].C(=O)([O-])[O-].[K+].[K+]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[NH2:42][C:33]1[CH:34]=[CH:35][C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:32]=1[C:50]1[CH:51]=[C:46]([CH:47]=[CH:48][CH:49]=1)[C:43]([OH:45])=[O:44]

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 108678611-Bromonaphthalen-2-amineHCID 86660564Disodium ethylenediaminetetraacetic acid dihydrate

Product 1

HCID 585687123-(2-Aminonaphthalen-1-yl)benzoic acid

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A freshly prepared solution of 112 mg (0.5 mmol) of palladium(II) acetate, 106 mg (1 mmol) of sodium carbonate and 186 mg (0.5 mmol) of ethylenediaminetetraacetic acid disodium dihydrate in 50 ml of water is added to a vigorously stirred mixture of 22.2 g (100 mmol) of 1-bromo-2-aminonaphthalene [20191-75-7], 18.3 g (110 mmol) of 3-carboxybenzeneboronic acid [25487-66-5], 27.6 g (200 mmol) of potassium carbonate and 645 mg (2 mmol) of tetrabutylammonium bromide in 300 ml of water, and the mixture is heated under reflux for 16 h. After cooling, the pH is adjusted to 3-4 by addition of acetic acid, and the solid is filtered off with suction, washed a number of times with 5% by weight acetic acid, dried in vacuo and then subjected to azeotropic drying with toluene. Yield: 23.8 g (90 mmol), 90.4%; purity according to 1H-NMR about 98%.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. filtrationthe solid is filtered off with suction
  5. washwashed a number of times with 5% by weight acetic acid
  6. customdried in vacuo
  7. dry with materialto azeotropic drying with toluene

Sources & evidence

ORD record
ord-20244e6486ef41158c45c3e3d958b5b1
Source dataset
uspto-grants-2015_07
Patent number
US09085579B2

Reaction notes

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