Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Methoxyaniline | HCID 7000 | — |
| Reactant | N-(3-Methoxypropyl)naphthalen-1-amine | HCID 88339 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 21698798 | HCID 21698798 | — |
Reaction Steps
To a three liter flask was charged 200 grams of ice and 1.25 moles of hydrochloric acid. 63.6 grams of o-anisidine was added. At a temperature of 0°-3° C. was added 35 gm of sodium nitrite as a 40% solution. Once the o-anisidine was fully diazotized, 100 gm. of methoxypropyl alpha naphthylamine and 100 gm of xylene were added. The pH was then raised to between 3.5 and 4.0 with a mineral alkaline buffering agent. The coupling temperature was maintained at between 8°-12° C. while the mixture was stirred for 4 hours until a negative coupling test was achieved. The reaction was heated to 70°C. An organic layer was separated from an aqueous phase. Xylene was stripped under vacuum. The non-volatile tarry substance was dissolved in an aromatic high flash solvent which is 50% product/50% viscosity depressant, which solution is stable at -20° C. indefinitely.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05490872 |
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| Source dataset | uspto-grants-1996_02 |
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| ORD ID | ord-fdf3c3b54a0e4017976f3beb5a4eb99d |
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| Source note | uspto-grants-1996_02 |
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