Anthranilic Acid → 4,4-Diaminodiphenylmethane

HRID 1071901Notes

Reaction equation

N[C:2]1[C:3]([C:8](O)=O)=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](C(O)=O)[CH:13]=1.[NH2:21]C1C=CC=CC=1.C=O>>[CH:2]1[C:3]([CH2:8][C:15]2[CH:14]=[CH:13][C:12]([NH2:11])=[CH:17][CH:16]=2)=[CH:4][CH:5]=[C:6]([NH2:21])[CH:7]=1

Participants

Reactant 4

HCID 227Anthranilic Acid

HCID 712Formaldehyde

HCID 6115Aniline

HCID 74193-Aminobenzoic Acid

Product 1

HCID 75774,4-Diaminodiphenylmethane

Procedure

An 2-anilinecarboxylic acid derivative (e.g. sodium 2-anilinecarboxylate) or an 3-anilinecarboxylic acid derivative (e.g. sodium 3-anilinecarboxylate) and aniline are treated with formalin under acidic conditions to give the corresponding 4,4′-diaminodiphenylmethane derivative. This is diazotized using sodium nitrite under acidic conditions in the presence of hydrochloric acid, followed by reaction with sodium azide, to give the desired product.

Sources & evidence

ORD record: ord-2ce00e80503d405ba2893def53c71c1c
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908719B1

Reaction notes

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