Hydrochloric Acid → 4-(2-{2-[(2-Hydroxy-1-naphthyl)diazenyl]phenoxy}ethyl)-4-methylmorpholin-4-ium chloride

HRID 2109963Notes

Reaction equation

HRID 2109963 reaction equation
COS([O-])(=O)=O.[NH2:7][C:8]1[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=1[O:10][CH2:11][CH2:12][N+:13]1([CH3:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.N([O-])=O.[Na+].[NH2:28]S(O)(=O)=O.[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[OH:43].C(=O)([O-])[O-].[Na+].[Na+].[ClH:50]>O.C(O)(C)C>[Cl-:50].[OH:43][C:34]1[CH:35]=[CH:36][C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]=1[N:28]=[N:7][C:8]1[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=1[O:10][CH2:11][CH2:12][N+:13]1([CH3:19])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 5987Sulfamic AcidHCID 86632-NaphtholHCID 10340Sodium CarbonateHCID 23668193Sodium Nitrite2×HCID 867608484-[2-(2-Aminophenoxy)ethyl]-4-methylmorpholin-4-ium methylsulfate

Product 1

HCID 1363346924-(2-{2-[(2-Hydroxy-1-naphthyl)diazenyl]phenoxy}ethyl)-4-methylmorpholin-4-ium chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

1.5 g (4.3 mmol) of the compound from Step 5.3 was dissolved in 30 mL of water and 1.3 g of 32% hydrochloric acid solution. At 0 to 5° C., 0.31 g (4.5 mmol) of sodium nitrite in 3 mL of water was added dropwise without allowing the temperature to exceed 5° C. After one hour of additional agitation in the ice bath, excess sodium nitrite was decomposed with sulfaminic acid, and the mixture was poured with agitation into a solution of 0.65 g (4.3 mmol) of 2-naphthol in 8 mL of isopropanol. To this mixture was added a saturated solution of sodium carbonate until the pH reached a value of 9. The mixture was then allowed to agitate for an additional 30 min after which it was neutralized with dilute hydrochloric acid and suction-filtered. The resulting crude product was suspended in 20 mL of 2-normal hydrochloric acid at room temperature for 15 minutes after which the mixture was suction-filtered and dried.

Workup

  1. customto exceed 5° C
  2. filtrationsuction-filtered
  3. waitThe resulting crude product was suspended in 20 mL of 2-normal hydrochloric acid at room temperature for 15 minutes
  4. filtrationafter which the mixture was suction-filtered
  5. customdried

Sources & evidence

ORD record
ord-3b5355a720e640daa6f0e5b67aef8941
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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