m-Aminoacetanilide → HCID 12143390, compound

HRID 485473Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])(=[O:3])[CH3:2].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH:8][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 7604m-Aminoacetanilide

HCID 81401-Bromooctane

HCID 11430Potassium Carbonate

Product 1

HCID 12143390HCID 12143390, compound

Procedure

3-Acetylaminoaniline (15 parts) was reacted with n-octyl bromide (19.3 parts) at 90° to 100° C. for 4 hours in the presence of anhydrous potassium carbonate (6.9 parts) to obtain 3-acetylamino-N-octylaniline. Thereafter, reaction was further continued at 120° to 130° C. for 4 hours with addition of n-hexyl bromide (16.5 parts) and anhydrous potassium carbonate (6.9 parts) to obtain 3-acetylamino-N-n-octyl-N-n-hexylaniline (coupling component). In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline was diazotized and coupled with the above coupling component to obtain 45.9 parts of a dye (5).

Sources & evidence

ORD record: ord-f93ac8d0a66245218b2828ec18964833
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04536569

Reaction notes

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