Hydrochloric Acid → HCID 66750577, compound

HRID 643867Notes

Reaction equation

HRID 643867 reaction equation
C(=[N:14][C:15]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:21]=2)[CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:26]([O:25][C:24]1[C:15]([NH2:14])=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[CH:19][CH:18]=2)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86624015HCID 86624015, compound

Product 1

HCID 66750577HCID 66750577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzhydrylidene-(3,6-bis-benzyloxynaphthalen-2-yl)-amine (0.628 g, 1.208 mmol) is dissolved in 15 mL of THF. A solution of 1 N HCl (15 mL) is added and stirred for 30 min. The crude reaction mixture is basified to pH 14 with 1 N NaOH and extracted with EtOAc. The combined organic layers are dried and evaporated to afford an orange oil. The oil is purified on silica, eluting with 9:1 hexanes/EtOAc and then 1:1 hexanes/EtOAc, to afford 3,6-bis-benzyloxynaphthalen-2-ylamine.

Workup

  1. customThe crude reaction mixture
  2. extractionextracted with EtOAc
  3. customThe combined organic layers are dried
  4. customevaporated
  5. customto afford an orange oil
  6. customThe oil is purified on silica
  7. washeluting with 9:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-d331e0c5df3c4b22982440782e89a14e
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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