Hydrochloric Acid → HCID 21698798, compound

HRID 2395912Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[C:5]([NH2:10])=[CH:6][CH:7]=[CH:8][CH:9]=1.[N:11]([O-])=O.[Na+].[CH3:15][O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C1(C)C(C)=CC=CC=1>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([NH:20][CH2:19][CH2:18][CH2:17][O:16][CH3:15])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

temperatureThe pH was then raised to between 3.5 and 4.0 with a mineral alkaline buffering agent
temperatureThe coupling temperature was maintained at between 8°-12° C. while the mixture
customAn organic layer was separated from an aqueous phase
dissolutionThe non-volatile tarry substance was dissolved in an aromatic high flash solvent which
customis stable at -20° C.

Sources & evidence

ORD record: ord-fdf3c3b54a0e4017976f3beb5a4eb99d
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05490872

Reaction notes

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